Ethyl 2-ethoxy-3-(4-hydroxy-3-methylphenyl)propanoate → 2-Ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid

HRID 1628154Notes

Reaction equation

HRID 1628154 reaction equation
C([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH3:14])[CH:8]=1)C.C(C1C=C(CC(OCC)C(O)=O)C=CC=1O)C1C=CC=CC=1>>[CH2:16]([O:15][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH3:14])[CH:8]=1)[C:4]([OH:18])=[O:3])[CH3:17]

Participants

3

Reactant 2

HCID 22708451Ethyl 2-ethoxy-3-(4-hydroxy-3-methylphenyl)propanoateHCID 668649833-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid

Product 1

HCID 226474722-Ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid

Procedure

The title compound was prepared from 2-ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid ethyl ester (0.85 g, 2.28 mmol) in the same manner as described for 3-(3-benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid. The crude product was used in the next step without further purification (0.71 g, 85%). 1H NMR (400 MHz, CDCl3): δ 6.98 (s, 1H), 6.90-6.93 (d, 1H), 6.64-6.66 (d, 1H), 4.03-4.07 (dd, 1H), 3.57-3.65 (m, 1H), 3.41-3.46 (m, 1H), 2.88-3.05 (ddd, 2H), 2.20 (s, 3H), 1.15-1.20 (t, 3H).

Workup

  1. customThe crude product was used in the next step without further purification (0.71 g, 85%)

Sources & evidence

ORD record
ord-8dfc8dd5bfd043d9b39d7337543538a8
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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