Phosgene → 2-Ethylbutyl carbonochloridate

HRID 328343

Reaction equation

HRID 328343 reaction equation
[CH2:1]([CH:3]([CH2:6][CH3:7])[CH2:4][OH:5])[CH3:2].[C:8](Cl)([Cl:10])=[O:9].ClC([O-])=O>C1C=CC=CC=1>[Cl:10][C:8]([O:5][CH2:4][CH:3]([CH2:6][CH3:7])[CH2:1][CH3:2])=[O:9]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 73582-Ethyl-1-butanolHCID 21226386Carbonochloridate

Product 1

HCID 544120422-Ethylbutyl carbonochloridate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20.4 G. (0.2 moles) of 2-ethyl-1-butanol is added dropwise under anhydrous conditions to 250 ml. (0.4 moles) of 17.2% phosgene solution in benzene with stirring in an ice bath. The addition is complete in 70 minutes and the solution is allowed to gradually warm to room temperature and stirred for 16 hours. The excess phosgene and hydrogen chloride are removed with a stream of nitrogen and the residual solution evaporated to dryness in vacuo affording 17.9 g. (54%) of a light yellow oil which IR demonstrates having a strong chloroformate band and no hydroxy. The oil is used as is in further reactions.

Workup

  1. additionThe addition
  2. customThe excess phosgene and hydrogen chloride are removed with a stream of nitrogen
  3. customthe residual solution evaporated to dryness in vacuo
  4. customaffording 17.9 g

Sources & evidence

ORD record
ord-efbfbebf66014f23bbf37360e380f506
Source dataset
uspto-grants-1977_04
Patent number
US04017505

Linked notes

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