Ethyl 2-[4-(2-benzyloxyethyl)phenoxy]-2-methylpropionate → Ethyl 2-[4-(2-hydroxy-ethyl)-phenoxy]-2-methyl-propionate

HRID 2121845Notes

Reaction equation

HRID 2121845 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]([CH3:22])([CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 15453494Ethyl 2-[4-(2-benzyloxyethyl)phenoxy]-2-methylpropionate

Product 1

HCID 15229879Ethyl 2-[4-(2-hydroxy-ethyl)-phenoxy]-2-methyl-propionateYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-[4-(2-benzyloxyethyl)phenoxy]-2-methylpropionate (480 mg) in ethanol (3.0 ml) was added 10% palladium on activated carbon (30 mg), and the mixture was stirred for 48 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and the solvent of the filtrate was removed under reduced pressure. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent:hexane/diethyl ether=1/1) gave ethyl 2-[4-(2-hydroxyethyl)phenoxy]-2-methylpropionate (310 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent:hexane/diethyl ether=1/1)

Sources & evidence

ORD record
ord-99d99ac2bd1e4ab6b09a18edc5e1833e
Source dataset
uspto-grants-2004_02
Patent number
US06696489B1

Reaction notes

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