Hydrochloric Acid → 4-(Chloromethyl)benzoic acid

HRID 2413534Notes

Reaction equation

HRID 2413534 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11]Cl.Cl>ClC1C=CC=CC=1>[Cl:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7470P-Toluic AcidHCID 24526Chlorine

Product 1

HCID 742344-(Chloromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

272 parts of 4-methyl-benzoic acid are dissolved in 750 parts of chlorobenzene at 100° C. and are chlorinated at this temperature by the introduction of elementary chlorine under UV light; the chlorination process is ended when 71 parts of hydrochloric acid have been formed. The reaction mixture is then cooled to about 0° C., with stirring, and the precipitate which has separated out is filtered off, freed from chlorobenzene by being washed several times with low-boiling petroleum ether and dried. 307 parts of 4-(chloromethyl)-benzoic acid with a melting point of 196° to 200° C. are obtained.

Workup

  1. customhave been formed
  2. customthe precipitate which has separated out
  3. filtrationis filtered off
  4. washby being washed several times with low-boiling petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-b88d54ed2651475399fda1103d8ca8c1
Source dataset
uspto-grants-1988_01
Patent number
US04719053

Reaction notes

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