Hydroxyphenylacetic acid → 4-Benzyloxyphenylacetic acid ethyl ester

HRID 2268453Notes

Reaction equation

HRID 2268453 reaction equation
CN([CH:4]=[O:5])C.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:25](=O)([O-])[O-].[K+].[K+]>O>[CH2:17]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([O:5][CH2:4][CH3:25])=[O:16])=[CH:11][CH:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 27374284-Benzyloxyphenylacetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A DMF (100 ml) suspension of 4-hydroxyphenylacetic acid (10.0 g, 55.5 mmols), benzyl bromide (7.93 ml, 66.6 mmols) and potassium carbonate (23.1 g, 167 mmols) was stirred at room temperature for 6 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane alone to hexane:ethyl acetate=10:1) to obtain the entitled compound (14.6 g) as an oil.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and then dried
  4. customThe solvent was evaporated out in vacuo
  5. customthe resulting crude product was purified by silica gel column chromatography (hexane alone to hexane

Sources & evidence

ORD record
ord-860093b5ec2149b08be6b63f182ac349
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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