Phosgene → Carbonochloridic acid, cyclohexyl ester

HRID 1249750Notes

Reaction equation

HRID 1249750 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:15](Cl)([Cl:17])=[O:16]>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:17][C:15]([O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:16]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 7966CyclohexanolHCID 8471Triethylamine

Product 1

HCID 83262Carbonochloridic acid, cyclohexyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of cyclohexanol (500 mg, 5.0 mmol) and triethylamine (836 μl) in methylene chloride (4 ml) was added to a 0° C. solution of phosgene in toluene (5.3 ml, 20%). The resultant mixture was stirred at 0° C. for 2.5 hours. TLC showed completion of the reaction. The solvent was removed and anhydrous ether (50 m l) was added. The mixture was filtered and the filtrate was concentrated to give 726 mg of the desired product as a colorless oil which was used without further purification. IR (film) 1776 cm−1.

Workup

  1. customcompletion of the reaction
  2. customThe solvent was removed
  3. additionanhydrous ether (50 m l) was added
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b966f7dd4e464adfa2c4192bbf647a9f
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

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