Hydrochloric Acid → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 1982244Notes

Reaction equation

HRID 1982244 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+].Cl>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 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl ethers may conveniently be used to protect --YH groups. For example, methyl 4-hydroxyphenylacetate (0.2 mol) is heated at reflux with 25 g benzyl chloride (0.2 mol) and 25 g K2CO3 (0.2 mol) in 100 ml ethanol. The product is added to dilute aqueous HCl, extracted with ether, and purified by silica gel chromatography to yield methyl 4-benzyloxyphenylacetate (7).

Workup

  1. extractionextracted with ether
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-75d9c71f5026420daa8db644de500ed6
Source dataset
uspto-grants-1986_06
Patent number
US04595690

Reaction notes

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