Diazomethane → Methyl 3-hydroxy-4-methylbenzoate

HRID 2255122Notes

Reaction equation

HRID 2255122 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[N+](=[CH2:14])=[N-]>C(OCC)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:14])=[O:6]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 685123-Hydroxy-4-methylbenzoic acid

Product 1

HCID 354091Methyl 3-hydroxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-hydroxy-4-methylbenzoic acid (26.1 g, 0.17 mol) in 200 mL of diethylether is treated with a solution of diazomethane in ether until a persistent yellow color develops. The resulting solution is stirred for 24 hours. The resulting solution is concentrated and the residue is crystallized from CH2Cl2. A white solid which is methyl 3-hydroxy-4-methylbenzoate is obtained (26.5 g, 93%).

Workup

  1. concentrationThe resulting solution is concentrated
  2. customthe residue is crystallized from CH2Cl2
  3. customis obtained (26.5 g, 93%)

Sources & evidence

ORD record
ord-70d0581add0e448db2aa7604603f0089
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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