Phosgene → 2-(Chloromethyl)benzoyl chloride

HRID 1582418Notes

Reaction equation

HRID 1582418 reaction equation
C1(C2C(=CC=CC=2)CO1)=O.[C:11]([Cl:14])(Cl)=[O:12].Cl[C:16]1[C:24](CC)=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([Cl:20])=O>N1C=CC=C(C)C=1.B(O)(O)O>[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 86759447HCID 86759447, compound

Product 1

HCID 30163952-(Chloromethyl)benzoyl chlorideYield 90%

Reagents, catalysts & solvents 2

HCID 7628Boric AcidCatalystHCID 79703-MethylpyridineCatalyst

Conditions

Temperature
140 °C

Procedure

268 g (2 mol) of phthalide, 9.3 g (0.1 mol) of β-picoline and 3.1 g (0.05 mol) of crystalline boric acid (Riedel de Haen) were initially charged. At 140-150° C., a total of 245 g (2.45 mol) of gaseous phosgene was introduced over a period of 7 h. The mixture was then stirred at 140° C. for another hour. Excess phosgene was stripped using nitrogen, giving a discharge of 380 g having a content of 96 GC area % of o-chloro-ethylbenzoyl chloride and 1.4% of unreacted phthalide. ractional distillation of the crude discharge gave 340 g of o-chloromethylbenzoyl chloride (90% of theory) of a purity of >97%.

Workup

  1. customgiving a discharge of 380 g
  2. distillationractional distillation of the crude discharge

Sources & evidence

ORD record
ord-4c712f84eb9840c59888ee6a74a20e34
Source dataset
uspto-grants-2004_05
Patent number
US06734322B1

Reaction notes

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