Hydrochloric Acid → 4-(Chloromethyl)benzaldehyde

HRID 569666Notes

Reaction equation

HRID 569666 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[ClH:11]>C1(C)C=CC=CC=1>[Cl:11][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5563304-(Hydroxymethyl)benzaldehyde

Product 1

HCID 3578774-(Chloromethyl)benzaldehydeYield 62.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g (0.132 moles) of 90 percent pure 4-hydroxymethylbenzaldehyde were stirred for 2 hours at 80° C. under an argon atmosphere with 50 ml of 37 percent HCl (0.58 moles) and 200 ml of toluene. After cooling to room temperature, the aqueous phase was separated off and the toluene phase was evaporated in vacuo. This gave 16.2 g of crude product which, according to NMR, contained 78.8% by weight of 4-chloromethylbenzaldehyde, 10% by weight of 1,4-bis-chloromethylbenzene and 11.2% by weight of an unknown substance. A 4-chloromethylbenzaldehyde yield of 12.8 g, corresponding to 62.5% of the theoretical yield was calculated from the NMR result.

Workup

  1. customthe aqueous phase was separated off
  2. customthe toluene phase was evaporated in vacuo

Sources & evidence

ORD record
ord-78f81ac9d93648d8a1e8e6cbddede379
Source dataset
uspto-grants-1988_03
Patent number
US04733012

Reaction notes

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