4-Hydroxybenzaldehyde → 4-Methoxybenzaldehyde

HRID 462138Notes

Reaction equation

HRID 462138 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.S(OC)(O[CH3:14])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].O>C1C=CC=CC=1>[CH3:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962Water2×HCID 6497Dimethyl SulfateHCID 10340Sodium Carbonate

Product 1

HCID 312444-MethoxybenzaldehydeYield 99.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20 g of p-hydroxybenzaldehyde (0.164 mol) was reacted with 29.0 g of dimethyl sulfate (0.230 mol) and 22.0 g of sodium carbonate (0.20 mol) for 2 hr. at 75°-80° C. A total of 12 ml of water was added in small portions over the last hour. Work-up by addition of water, acidification and benzene extraction yielded 22.27 g of p-methoxybenzaldehyde (99.9%) containing not more than 0.1% p-hydroxybenzaldehyde.

Workup

  1. customat 75°-80° C

Sources & evidence

ORD record
ord-2730ca5b31fa47ae95b61af418b12d1a
Source dataset
uspto-grants-1977_12
Patent number
US04065504

Reaction notes

Loading…