(E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate → Ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate

HRID 2101762Notes

Reaction equation

HRID 2101762 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[CH3:22])/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 12235562(E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 20748401Ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The reaction mixture compound 12.2 (2.80 g, 9.45 mmol) and Pd/C (0.40 g, wt 10% on activated carbon) in EtOH (35 mL) was purged with hydrogen three times and stirred under hydrogen at ambient temperature overnight. The catalyst was removed by filtration. The filtrate was evaporated to give the crude compound 12.3 which was used in the next step without further purification. MS ESI (pos.) m/e: 209 (M+H). 1H NMR (CDCl3) δ 7.02(d, 2H), 6.75(d, 2H), 4.11(q, 2H), 2.93(dd, 1H), 2.68(m, 2H), 1.21(t, 3H), 1.16(d, 3H).

Workup

  1. customThe catalyst was removed by filtration
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-dd8d12015de648a9a8a908529d6ab245
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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