Water → HCID 86753386, compound

HRID 1455984Notes

Reaction equation

HRID 1455984 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[C:4]([OH:11])[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:12]([O:11][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[C:8]([O:10][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 57882-Hydroxy-p-toluic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 86753386HCID 86753386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methylsalicyclic acid (20 g), benzylbromide (33 ml) and potassium carbonate (36.3 g ) in DMF (100 ml) was stirred for 12 hours. The mixture was poured into water (300 ml) and extracted three times with diethylether (100 ml each time). The combined organic extracts were washed with water and dried. Removal of the solvent gave benzyl 2-benzyloxy-4-methylbenzoate acid as a yellow liquid, yield 45 g.

Workup

  1. extractionextracted three times with diethylether (100 ml each time)
  2. washThe combined organic extracts were washed with water
  3. customdried
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-a186e322001a4fa5a64c70f4ed075764
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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