Ethyl 3-(4-benzyloxyphenyl)but-2-enoate → Ethyl 3-(4-hydroxyphenyl)butanoate

HRID 581004Notes

Reaction equation

HRID 581004 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:22])=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 53681599Ethyl 3-(4-benzyloxyphenyl)but-2-enoate

Product 1

HCID 51349438Ethyl 3-(4-hydroxyphenyl)butanoateYield 63.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-(4-benzyloxyphenyl)but-2-enoate (3.4 g) in ethyl acetate (100 ml) was hydrogenated over a 10% palladium-on-carbon catalyst (250 mg) at atmospheric pressure/ambient temperature. The catalyst was removed by filtration and the filtrate evaporated to give an oil. The oil was purified by chromatography on silica gel using a 4/1 (v/v) mixture of hexane and ethyl acetate as eluent to give ethyl 3-(4-hydroxyphenyl)butanoate (1.51 g) as a pale yellow oil; NMR(CDCl3): 1.20(3H,t), 1.27(3H,d), 2.52(2H,q), 3.22(1H,m), 4.08(2H,q), 4.84(1H,s), 6.71(2H,m) and 7.08(2H,m); m/z 208(M). Ethyl 3-(4-allyloxyphenyl)butanoate was prepared using the procedue used to prepare ethyl 3-(4-allyloxyphenyl)propionate (see Example 1) but using ethyl 3-(4-hydroxyphenyl)butanoate in place of ethyl 3-(4-hydroxyphenyl)propionate; NMR(CDCl3) 1.17(3H,t), 1.25(3H,d), 2.51(2H,m), 3.22(1H,m), 4.05(2H,q), 4.50(2H,m), 5.33(2H,m), 6.06(1H,m), 6.82(2H,m) and 7.11(2H,m); m/z 249 (M+H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customto give an oil
  4. customThe oil was purified by chromatography on silica gel using
  5. additiona 4/1 (v/v) mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-a4223fcd448740f2a06d65448f4f25bd
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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