Vanillin → Vanillin acetate

HRID 448179Notes

Reaction equation

HRID 448179 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[CH3:12][C:13](OC(C)=O)=[O:14]>C1COCC1>[C:13]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11])(=[O:14])[CH3:12]

Participants

4

Reactant 2

HCID 1183VanillinHCID 7918Acetic Anhydride

Product 1

HCID 61229Vanillin acetateYield 117%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of of 4-hydroxy-3-methoxybenzaldehyde (10 g, 66 mmol) in 30 mL of THF was added Ac2O (8 g, 80 mmol) and TEA (20 g, 198 mmol). The reaction was stirred at room temperature overnight. The volatiles were evaporated to afford 15 g of product as an oil, which was used for next step without further purification.

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-7d3d3d01d5e34a9c900222d2089daede
Source dataset
uspto-grants-2013_07
Patent number
US08481590B2

Reaction notes

Loading…