2-Chlorobenzoic Acid → 2-Chlorobenzoyl chloride

HRID 641889Notes

Reaction equation

HRID 641889 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].O=S(Cl)[Cl:13]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:13])=[O:5]

Participants

4

Reactant 2

HCID 83742-Chlorobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 691102-Chlorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

Into a 500 mL round bottom flask was placed a solution of 2-chlorobenzoic acid (20 g, 127.80 mmol) in toluene (150 mL). To the mixture was added SOCl2 (16 g, 134.45 mmol). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 75° C. in a bath of oil. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 22.3 g (100%) of 2-chlorobenzoyl chloride as yellow oil.

Workup

  1. customInto a 500 mL round bottom flask was placed
  2. customto react
  3. concentrationThe mixture was concentrated by evaporation under vacuum
  4. customa rotary evaporator
  5. customThis resulted in 22.3 g (100%) of 2-chlorobenzoyl chloride as yellow oil

Sources & evidence

ORD record
ord-dbb8268b021d477e8dfd2219a4e0f040
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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