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Process for preparing hydroxytyrosol
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A technology of hydroxytyrosol and hydroxyethyl, applied in the field of preparation of hydroxytyrosol, can solve the problems of safrole being expensive, expensive and complicated
Inactive Publication Date: 2015-06-17
LONZA GUANGZHOU NANSHA LTD
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[0010] In summary, the methods known in the art for the preparation of hydroxytyrosol by organic synthesis tend to be cumbersome and expensive
Furthermore, these methods use starting materials that are often not readily available
Some reactions require high temperature or pressure, which further increases energy consumption and cost
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example 1
[0057] Example 1: Preparation of 4-(2-hydroxyethyl)-2-methoxyphenol from eugenol (12)
[0058] Ozone gas was bubbled into eugenol (5.0 g, 30.5 mmol) and a catalytic amount of NaHCO in methanol-dichloromethane (1:1, 200 mL) at -78 °C 3 (0.1 g) solution. After stirring at this temperature for 2.0 hours, the ozone was replaced by nitrogen. After 15 minutes, NaBH 4 (1.21 g, 32 mmol, 1.05 eq) was added in part to the reaction mixture. When the addition was complete, the dry ice-acetone bath was removed, and the reaction mixture was slowly warmed to room temperature. After stirring at room temperature for 2 hours, the solvent was evaporated under reduced pressure. Brine (100ml) was added and the resulting mixture was extracted with ethyl acetate (3 x 100ml). The organic extract was dried over anhydroussodiumsulfate and concentrated to give an orange oil (4.0 g, 80%). 1 H NMR (400 MHz, DMSO-d6): δ 8.64 (br s, 1H), 6.76 (d, J=2.0 Hz, 1H), 6.66 (d, J=8.0 Hz, 1H), 6.58 (dd, J =...
example 2
[0059] Example 2: Preparation of Hydroxytyrosol from 4-(2-Hydroxyethyl)-2-Methoxyphenol (12)
[0060] To a stirred solution of aluminum chloride (3.1 g, 23.3 mmol, 4.0 equiv) in ethanethiol (16 mL) cooled in an ice-water bath was added 4-(2-hydroxy-ethyl)-2-methoxy Phenol (0.99 g, 5.9 mmol). The reaction was stirred at 0°C for 2 hours and at room temperature for 40 hours. The reaction was poured into ice water (50 mL) and acidified with dilute HCl (10 mL). Ethanthiol was removed by evaporation, and brine was added. The mixture was extracted with ethyl acetate (3 x 20ml). The combined extracts were dried over anhydroussodiumsulfate and concentrated to give a red oil (0.86 g, 94.7%). 1 H NMR (400 MHz, DMSO-d6): δ 8.69 (br s, 1H), 8.59 (br s, 1H), 6.60 (d, J=7.8 Hz, 1H), 6.58 (d, J=2.0 Hz, 1H), 6.42 (dd, J=7.8, 2.0 Hz, 1H), 4.55 (t, J=5.2 Hz, 1H, -OH), 3.50 (m, 2H), 2.53 (t, J=7.3 Hz, 2H) . 13C NMR (100 MHz, DMSO-d6): δ 144.9, 143.4, 130.31, 119.6, 116.4, 115.5, 62.7, 38...
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Abstract
A process for preparing hydroxytyrosol from eugenol is disclosed. The eugenol can be converted to 4-(2-hydroxyethyl)-2-methoxyphenol, which is subsequently converted to hydroxytyrosol. The eugenol can also be initially demethylated, and the reaction product is subsequently converted to hydroxytyrosol. A process for producing 4-(2-hydroxyethyl)-2-methoxyphenol is also disclosed.
Description
technical field [0001] The present invention relates to a process for the preparation of hydroxytyrosol from eugenol. The invention also relates to a process for the preparation of 4-(2-hydroxyethyl)-2-methoxyphenol. Background technique [0002] Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET, CAS10597-60-1) is a phytochemical with strong antioxidant properties. In nature, hydroxytyrosol is found in olive oil as its elemate methyl oleuropein, especially when degraded, in its ordinary form. Olives, olive leaves and olive pulp contain small amounts of hydroxytyrosol, which can be recovered to prepare hydroxytyrosol extracts. Hydroxytyrosol has been shown to be a monoamine oxidase inhibitor (MAOI). It acts as a potent monoamine oxidase B inhibitor. Hydroxytyrosol is also a metabolite of the neurotransmitterdopamine. The pharmacological effects of hydroxytyrosol are anti-inflammatory, vasodilatory, antihypertensive, antimicrobial and fungicidal properties. Hydroxytyros...
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