Phenol → Phenyl chloroformate

HRID 2083261Notes

Reaction equation

HRID 2083261 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN(C)C(N(C)C)=O>>[C:5]1([O:11][C:1]([Cl:4])=[O:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 6371Phosgene3×HCID 12437Tetramethylurea

Product 1

HCID 15891Phenyl chloroformateYield 99%

Conditions

Temperature
120 °C

Procedure

In a reaction vessel provided with stirrer, thermometer and introduction tube for phosgene, a mixture of 94 g of phenol and 4.4 g of N,N,N',N'-tetramethyl urea were heated at 120° C and phosgene was led through at a speed of 100 g per hour. The introduction of phosgene was interrupted after 5 hours and the reaction mixture was distilled. 144 g (=92% of the theoretical amount) of a 99% chloroformic acid phenyl ester were obtained.

Workup

  1. customIn a reaction vessel provided with stirrer
  2. distillationthe reaction mixture was distilled

Sources & evidence

ORD record
ord-12971bd293f64bc3b3b73aebd2c1a935
Source dataset
uspto-grants-1978_04
Patent number
US04085129

Reaction notes

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