Phenol → Phenyl chloroformate

HRID 1902820Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](Cl)([Cl:10])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:1]1([O:7][C:8]([Cl:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 996Phenol

HCID 6371Phosgene

HCID 11776Triphenylphosphine

Product 1

HCID 15891Phenyl chloroformateYield 90.6%

Procedure

The distillation residue is re-used with 500 g of phenol and 540 g of phosgene, without the use of fresh triphenylphosphine. After a phosgenation time of 10 hours, 754 g of distilled chloroformic acid phenyl ester are obtained (purity 99.8%; yield 90.4% of the theoretical yield).

Sources & evidence

ORD record: ord-58002b4183d443eb867c4483a4d2b0b7
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04366102

Reaction notes

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