3-Chloro-1-propanol → Butanoic acid, 3-oxo-, 3-chloropropyl ester

HRID 1194491Notes

Reaction equation

HRID 1194491 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]=[C:7]1[O:11][C:9](=[O:10])[CH2:8]1>C(N(CC)CC)C>[C:9]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:10])[CH2:8][C:7]([CH3:6])=[O:11]

Participants

4

Reactant 2

HCID 123133-Chloro-1-propanolHCID 12661Diketene

Product 1

HCID 10511540Butanoic acid, 3-oxo-, 3-chloropropyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-Chloropropanol (47.3 g, 0.50 mole) and a catalytic amount of triethylamine at 65° were treated dropwise with 42 g (0.50 mole) of diketene. After the addition was complete, the reaction was stirred at 65° for an additional hour. Distillation of the residue furnished 72.9 g (82%) of product as a clear liquid, b.p. 78°-85° at 150 mm.

Workup

  1. additionAfter the addition
  2. distillationDistillation of the residue

Sources & evidence

ORD record
ord-1b16592883a14a08b37e140f1a0ed86f
Source dataset
uspto-grants-1989_03
Patent number
US04814455

Reaction notes

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