Acetyl chloride → 4-[acetyloxy-methyl]benzaldehyde

HRID 1788920Notes

Reaction equation

HRID 1788920 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl>[C:18]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 5563304-(Hydroxymethyl)benzaldehyde

Product 1

HCID 5395854-[acetyloxy-methyl]benzaldehydeYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

54.2 g of 4-hydroxymethylbenzaldehyde, together with 40 g of triethylamine, are dissolved in 350 ml of dichloromethane. After the dropwise addition of 31.2 g of acetyl chloride at 0° to 5° C., the reaction mixture is allowed to stand overnight at room temperature. Thereafter, the precipitated triethylammonium chloride is filtered off under suction, and the filtrate is extracted 3 times with saturated bicarbonate solution. After it has been dried with sodium sulphate, the residue is distilled in a high vacuum. 47.9 g of a colorless solid are obtained in this manner.

Workup

  1. filtrationThereafter, the precipitated triethylammonium chloride is filtered off under suction
  2. extractionthe filtrate is extracted 3 times with saturated bicarbonate solution
  3. dry with materialAfter it has been dried with sodium sulphate
  4. distillationthe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-d376c969a22a4ad9a4185fd147ab4198
Source dataset
uspto-grants-1987_08
Patent number
US04686229

Reaction notes

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