Phosgene → o-sec-Butylphenyl chloroformate

HRID 2083263Notes

Reaction equation

HRID 2083263 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([CH2:7][CH3:8])[CH3:6].CN(C)C(N(C)C)=O>>[CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:1]([Cl:4])=[O:2])([CH2:7][CH3:8])[CH3:6]

Participants

4

Reactant 3

HCID 6371Phosgene3×HCID 69842-sec-ButylphenolHCID 12437Tetramethylurea

Product 1

HCID 3016372o-sec-Butylphenyl chloroformateYield 97%

Conditions

Temperature
100 °C

Procedure

In a round flask provided with stirrer, thermometer, an introduction tube for phosgene and a reflux cooler operating at about -30° C a mixture of 150 g of o-sec.-butylphenol and 4 g of N,N,N',N',-tetramethyl urea was heated at 100° C and phosgene was introduced to such a degree that the phosgene reflux in the deep-freezing cooler did not increase so much as to reduce the sump temperature. After a reaction time of about 5 hours and a phosgene consumption of about 190 g the reflux cooler was replaced by a descending cooler so that the greatest part of the excess phosgene could be separated from the reaction mixture by distillation. The rest of phosgene was blown out with dry nitrogen. Thus, a yield of about 97% of chloroformic acid-o-sec.-butyl-phenyl-ester was obtained which was practically free from the starting product (GC).

Workup

  1. customIn a round flask provided with stirrer
  2. temperaturereflux in the deep-freezing cooler
  3. temperaturedid not increase so much as
  4. customAfter a reaction time of about 5 hours and a phosgene consumption of about 190 g the reflux cooler
  5. customcould be separated from the reaction mixture by distillation

Sources & evidence

ORD record
ord-0b051d0a67eb4ffab9a74e8ad4b9d465
Source dataset
uspto-grants-1978_04
Patent number
US04085129

Reaction notes

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