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Method for synthesizing 4-tert-butyl benzaldehyde

A technology of tert-butylbenzaldehyde and its synthesis method, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., and can solve the problems of easy fire and high cost of safety control

Active Publication Date: 2020-02-04
HUBEI JINGHONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of highly active tert-butyllithium in this reaction is prone to fire during production scale-up, and the cost of safety control is very high. Refer to Journal of the American Chemical Society.1995, 117, 9091-9092.

Method used

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  • Method for synthesizing 4-tert-butyl benzaldehyde
  • Method for synthesizing 4-tert-butyl benzaldehyde
  • Method for synthesizing 4-tert-butyl benzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0019]

[0020] Under nitrogen protection, 106 g (1 mol) of benzaldehyde, 5 g of anhydrous p-toluenesulfonic acid and 500 g of methanol were put into the reaction flask. Raise the temperature to 40°C, add 111g (1.05mol) of trimethyl orthoformate dropwise, reflux and stir for 2 hours after the dropwise addition, after sampling and quenching, GC detects that there is no remaining benzaldehyde raw material, change to an atmospheric distillation device, and evaporate most of the ethanol . The system was cooled to 45-55°C to start vacuum distillation (-0.095--0.098Mpa), and finally distilled at 85-90°C to obtain 143g of colorless oily benzaldehyde dimethyl acetal, GC: 98.8%, yield: 93.7%. 1 HNMR (400MHz, CDCl 3 )δ:3.59(s,6H),5.79(d,1H),7.45-7.72(m,5H).

Embodiment 2

[0022]

[0023] Under nitrogen protection, 106 g (1 mol) of benzaldehyde, 5 g of anhydrous p-toluenesulfonic acid and 500 g of ethanol were put into the reaction flask. Raise the temperature to 40°C, add 156g (1.05mol) of triethyl orthoformate dropwise, reflux and stir for 2 hours after the dropwise addition, after sampling and quenching, GC detects that there is no remaining benzaldehyde raw material, change to an atmospheric distillation device, and evaporate most of the methanol . Cool the system to 49-58°C and start vacuum distillation (-0.095--0.098Mpa), and finally distill at 85-90°C to obtain 169g of colorless oily product benzaldehyde diacetal, GC: 98.5%, yield: 94.2% . 1 HNMR (400MHz, CDCl 3 )δ:1.22(s,6H),3.57(s,4H),5.79(d,1H),7.36-7.59(m,5H).

[0024] The second step: the synthesis of 4-tert-butylbenzaldehyde.

Embodiment 3

[0026]

[0027] 76 g (0.5 mol) of benzaldehyde dimethyl formal and 6.1 g of triphenylboron were put into the reaction flask. Under the cooling of circulating water, 42g (0.75mol) of isobutylene was introduced into the bottom tube, the reaction exothermic, the temperature was controlled at 30-35°C, and the reaction was carried out for 6 hours. After sampling and quenching, GC detected that there was no remaining raw material of benzaldehyde dimethyl acetal, and the system was cooled to 15-20°C, add 200g water and 1mol hydrochloric acid dropwise to adjust the pH=2-3, extract twice with 150mL ethyl acetate, combine the organic phases, concentrate under reduced pressure until no liquid remains, add toluene with a small amount of water until KF1 HNMR (400MHz, CDCl3) δ: 1.37(s, 9H), 7.56(d, 2H), 7.83(d, 2H), 9.56(s, 1H).

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Abstract

The invention discloses a method for synthesizing 4-tert-butyl benzaldehyde and belongs to the technical field of organic synthesis. The method comprises the steps of subjecting benzaldehyde and triorthoformate to a reaction to produce benzaldehyde acetal, then, subjecting the benzaldehyde acetal and isobutene to a sealed reaction in the presence of a catalyst, and carrying out acid quenching, thereby obtaining the 4-tert-butyl benzaldehyde. According to the method, the 4-tert-butyl benzaldehyde is obtained through adopting benzaldehyde protection, then, firstly, becoming an electron donatingorientating group, and then, prompting selective localization of the isobutene by employing an appropriate catalyst; and a ratio of a 2-tert-butyl benzaldehyde isomer to the product is smaller than 1:14, and after the reaction ends up, the process is applicable to industrialized large-scale production.

Description

technical field [0001] The invention relates to a synthesis method of 4-tert-butylbenzaldehyde, which belongs to the technical field of organic synthesis. Background technique [0002] 4-tert-butylbenzaldehyde, p-tert-butylbenzaldehyde, also known as 4-tert-butylbenzaldehyde, English name is p-TertbutylBenzaldehyde, molecular formula is C 11 h 14 O, with a molecular weight of 162.2283 and a CAS of 939-97-9, is used to synthesize spices, medicines, dyes, etc. At present, there are many synthetic methods for this product literature, mainly including: [0003] Using 4-tert-butyltoluene and 2-iodylbenzoic acid in fluorobenzene / DMSO, reacted at 80°C for 8h to obtain 4-tert-butylbenzaldehyde with a yield of 95%, Journal of the American Chemical Society.2002, 124, 2245-2258; or react with cerium amine nitrate in acetic acid at 85-95°C for 1.5h to obtain 4-tert-butylbenzaldehyde with a yield of 94%. JournalofOrganic Chemistry.1982, 47, 1647-1652. Or use 4-tert-butyl benzyl alcoh...

Claims

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Application Information

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IPC IPC(8): C07C45/51C07C47/542C07C41/56C07C41/48C07C43/307
CPCC07C45/515C07C41/56C07C41/48C07C47/542C07C43/307
Inventor 陈晨杨辉赵亚运黄新松
Owner HUBEI JINGHONG CHEM
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