Benzyl Chloride → Methyl 2-(2-(benzyloxy)phenyl)acetate

HRID 247720Notes

Reaction equation

HRID 247720 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:13]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 89719Methyl (2-hydroxyphenyl)acetate

Product 1

HCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetateYield 67.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15 g of methyl 2-hydroxyphenylacetate are refluxed with 11.4 g of benzyl chloride and 6.2 g of potassium carbonate in 90 ml of absolute methanol for 24 hours. The mixture is filtered, the filtrate is evaporated down, 400 ml of ether are added to the residue, and the solution is washed with water, dried with MgSO4 and evaporated down. Distillation of the residue at about 200° C. and under 18 mbar gives 15.5 g of pale oil.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated down
  3. addition400 ml of ether are added to the residue
  4. washthe solution is washed with water
  5. dry with materialdried with MgSO4
  6. customevaporated down
  7. distillationDistillation of the residue at about 200° C.

Sources & evidence

ORD record
ord-a523361b85824f5bbab73a2b0bfca2e6
Source dataset
uspto-grants-1987_11
Patent number
US04709078

Reaction notes

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