Vanillin → Vanillin acetate

HRID 1184968Notes

Reaction equation

HRID 1184968 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 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-1c5108c78c0045f8ac0b2fa2d43aeb6c
Source dataset
uspto-grants-2014_03
Patent number
US08669381B2

Reaction notes

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