2-Ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid → 2-Ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid benzyl ester

HRID 709472Notes

Reaction equation

HRID 709472 reaction equation
C(OC(CC1C=CC(O)=C(C)C=1)C(O)=O)C.[CH2:17]([O:24][C:25](=[O:45])[CH:26]([O:42][CH2:43][CH3:44])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35]C2C=CC=CC=2)[CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][C:25](=[O:45])[CH:26]([O:42][CH2:43][CH3:44])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH3:35])[CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 226474722-Ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acidHCID 668645693-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester

Product 1

HCID 668649262-Ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid benzyl ester

Procedure

The title compound was prepared from 2-ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid (0.71 g, 3.15 mmol) in the same manner as described for 3-(3-benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester. The crude product was purified by column chromatography using n-heptane/EtOAc (3:2) as the eluent and the title compound was obtained as an oil (0.51 g, 51.6%). 1H NMR (400 MHz, CDCl3): δ 7.26-7.38 (m, 5H), 6.96 (s, 1H), 6.97-6.91 (d, 1H), 6.65-6.67 (d, 1H), 5.16 (s, 2H), 4.08-4.12 (t, 1H), 3.61-3.66 (m, 1H), 3.39-3.44 (m, 1H), 2.96-2.99 (d, 2H), 2.20 (s, 3H), 1.17-1.22 (t, 3H).

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-96eecb7e727445ed89e00436fb161910
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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