4-Hydroxybenzoic Acid → Methyl anisate

HRID 1262735Notes

Reaction equation

HRID 1262735 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].S([O:21][CH3:22])(OC)=O>>[CH3:11][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:21][CH3:22])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 69223Dimethyl sulfite

Product 1

HCID 8499Methyl anisateYield 110%

Conditions

Temperature
100 °C

Procedure

To a 100 ml three-necked flask equipped for reflux and fitted with a mechanical stirrer was added 2.0 g (0.014 mol) of p-hydroxybenzoic acid, 1.0 g. (0.007 mol) of potassium carbonate, and 5.0 ml (0.059 mol) of dimethyl sulfite. The mixture was heated at 100° C. for four hours and then quenched with 15 ml of water. The organics were taken up with methylene chloride and washed sequentially with 12% caustic solution and water. The extracts were concentrated in vacuo to give 1.28 g of methyl p-methoxybenzoate.

Workup

  1. customTo a 100 ml three-necked flask equipped
  2. temperaturefor reflux
  3. customfitted with a mechanical stirrer
  4. customquenched with 15 ml of water
  5. washwashed sequentially with 12% caustic solution and water
  6. concentrationThe extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-c2ee80a52f3344439606b4e629e082fd
Source dataset
uspto-grants-1984_06
Patent number
US04453018

Reaction notes

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