Acetic Anhydride → 2-Acetoxy-3-methoxybenzaldehyde

HRID 218269Notes

Reaction equation

HRID 218269 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:12]([CH:13]=[O:14])[C:11]=1[OH:18].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:1]([O:18][C:11]1[C:10]([O:9][CH3:8])=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8991o-VanillinHCID 11430Potassium Carbonate

Product 1

HCID 2517032-Acetoxy-3-methoxybenzaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (45.9 g, 0.45 mol) was added to a suspension of 3-methoxysalicylaldehyde (45.6 g, 0.3 mol) and K2CO3 (42.0 g, 0.6 mol) in CH2Cl2 (450 L) at rt. The reaction mixture was stirred at rt overnight then filtered, evaporated and the residue was recrystallised from cyclohexane to give 42 (42.0 g, 74%) as colourless needles:

Workup

  1. filtrationthen filtered
  2. customevaporated
  3. customthe residue was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-e4efdb52c67c4a0e99b2eef199743808
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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