Ethyl 2-(2-fluoro-4-benzyloxyphenoxy)propionate → Ethyl 2-(2-fluoro-4-hydroxyphenoxy)propionate

HRID 542089Notes

Reaction equation

HRID 542089 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([O:16]CC2C=CC=CC=2)[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7]>[Pd].C(O)C>[F:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 13578008Ethyl 2-(2-fluoro-4-benzyloxyphenoxy)propionate

Product 1

HCID 13578009Ethyl 2-(2-fluoro-4-hydroxyphenoxy)propionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on charcoal (1.5 g) was added to a solution of ethyl 2-(2-fluoro-4-benzyloxyphenoxy)propionate (13 g) in ethanol (250 ml) and the stirred suspension was placed under hydrogen at atmospheric pressure for 2 hours. The catalyst was removed by filtration and the filtrate evaporated under reduced pressure to give the product, ethyl 2-(2-fluoro-4-hydroxyphenoxy)propionate, as a colourless oil (8.9 g, 95%). Proton magnetic resonance spectrum (CDCl3, δ in ppm): 1.3, t, 3H (CH2CH3); 1.6, d, 3H (--CHCH3); 4.25, q, 2H (OCH2CH3); 4.7, q, 1H (--CHCH3); 6.4-7.1, m, 4H (OH and phenoxy ring).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-b98eb5d532e142388f5531f4227df37d
Source dataset
uspto-grants-1987_04
Patent number
US04655819

Reaction notes

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