Benzyl Chloride → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 34404

Reaction equation

HRID 34404 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)C>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-hydroxyphenylacetate (5, 0.2 mol), obtainable from Aldrich Chemical Co. Inc., Milwaukee, Wis., is heated at reflux with benzyl chloride (25 g, 0.2 mol) and K2CO3 (25 g, 0.2 mol) in 100 mL ethanol. The product is added to dilute aqueous NaOH, extracted with ether, and purified by silica gel chromatography to yield methyl 4-benzyloxyphenylacetate (6). (Scheme II, Step 1.)

Workup

  1. temperature, is heated
  2. extractionextracted with ether
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9c76812738bd47cb8d4850477591476a
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Linked notes

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