Phosgene → 2-(Chloromethyl)benzoyl chloride

HRID 1582417Notes

Reaction equation

HRID 1582417 reaction equation
C1(C2C(=CC=CC=2)CO1)=O.[C:11]([Cl:14])(Cl)=[O:12].Cl[C:16]1[C:24](C)=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([Cl:20])=O>C1C=CC(P(C2C=CC=CC=2)(C2C=CC=CC=2)=O)=CC=1.B(F)(F)F>[Cl:20][CH2:18][C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[C:11]([Cl:14])=[O:12]

Participants

6

Reactant 3

HCID 6371Phosgene2×HCID 6885Phthalide2×HCID 193679402-Chloro-3-methylbenzoyl chloride

Product 1

HCID 30163952-(Chloromethyl)benzoyl chlorideYield 96%

Reagents, catalysts & solvents 2

HCID 6356Boron trifluorideCatalystHCID 13097Triphenylphosphine OxideCatalyst

Procedure

2 mol of phthalide (268 g) were initially charged with 27.8 g of TPPO (0.1 mol) and 7.9 g (0.04 mol) of BF3 etherate. At 140-150° C., a total of 233 g of gaseous phosgene (2.33 mol) were introduced over a period of 8 h. After an extra stirring time of 1 h at 140° C., the excess phosgene was stripped using nitrogen. The discharge (415 g) contained 88.4 GC area % of o-chloro-methylbenzoyl chloride and 0.1% of phthalide. Fractional distillation of the crude discharge gave 363 g (96% of theory) of o-chloromethylbenzoyl chloride of a purity of 99.8%.

Workup

  1. customAfter an extra stirring time of 1 h
  2. customat 140° C.
  3. distillationFractional distillation of the crude discharge

Sources & evidence

ORD record
ord-ef930ba9749f46ca894e37d2a5054418
Source dataset
uspto-grants-2004_05
Patent number
US06734322B1

Reaction notes

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