HCID 12134925, compound → Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionate

HRID 1393397Notes

Reaction equation

HRID 1393397 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:21])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:29])[C:5]([CH3:21])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 12134925HCID 12134925, compound

Product 1

HCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Phenoxy-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester (830 mg, 2.1 mmol) was dissolved in ethyl acetate (30 mL) and treated with 5% palladium on carbon (300 mg), and then stirred under an atmosphere of hydrogen for 20 h. The suspension was filtered through celite and concentrated in vacuo to produce 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionic acid ethyl ester colorless oil (563 mg, 89%) 1H NMR (300 MHz, CDCl3): δ 7.23 (t, 2H), 7.13 (d, 2H), 6.96 (t, 1H), 6.83 (d, 2H), 6.76 (d, 2H), 4.19 (q, 1H, J=7.1), 3.23 (d, 1H, J=12.4), 3.08 (d, 1H, J=12.4), 1.39 (s, 3H), 1.22 (t, J=7.1). MS [EI+] 318 (M+H)+, [EI−] 359 (M+OAc−).

Workup

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89f6c124ad264de1a1807f7537e4f6d8
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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