Acetic Anhydride → 2-Acetoxy-3-methoxybenzaldehyde

HRID 1836794Notes

Reaction equation

HRID 1836794 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].CN(C1C=CC=CN=1)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>Cl>[C:21]([O:5][C:4]1[C:6]([O:7][CH3:8])=[CH:9][CH:10]=[CH:11][C:3]=1[CH:2]=[O:1])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8991o-VanillinHCID 218852-Dimethylaminopyridine

Product 1

HCID 2517032-Acetoxy-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of o-vanillin (10.1 g) and a catalytic quantity (0.8 g) of dimethylaminopyridine in N-diisopropylethyl amine (23 mL) at 0° C. was added acetic anhydride (8 mL). The solution was stirred overnight, poured into 2N hydrochloric acid (100 mL), extracted with dichloromethane and the solvent removed in vacuo to afford a yellow solid. Recrystallization from ethanol yielded yellow crystals (10.9 g, 85%): m.p. 75.4-76.2° C., lit17 m.p. 76° C.; EIMS m/z 194 (M+), 152, 106, 43.

Workup

  1. extractionextracted with dichloromethane
  2. customthe solvent removed in vacuo
  3. customto afford a yellow solid
  4. customRecrystallization from ethanol yielded yellow crystals (10.9 g, 85%)

Sources & evidence

ORD record
ord-6b9024bc3b2949aa9c629344e94e9e1a
Source dataset
uspto-grants-2004_08
Patent number
US06777578B2

Reaction notes

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