Pyridine → (4-Nitrophenyl)methyl 4-chloro-3-oxobutanoate

HRID 1589620

Reaction equation

HRID 1589620 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[Cl:18][CH2:19][C:20](=[O:25])[CH2:21][C:22](Cl)=[O:23]>C(Cl)Cl>[Cl:18][CH2:19][C:20](=[O:25])[CH2:21][C:22]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 692754-Nitrobenzyl alcoholHCID 30162624-Chloro-3-oxobutyryl chloride

Product 1

HCID 20196963(4-Nitrophenyl)methyl 4-chloro-3-oxobutanoateYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After 191.2 g (1.25 mol) of p-nitrobenzyl alcohol is dissolved in 250 ml of methylene chloride, 98.8 g of pyridine is added, and the mixture is cooled to -5° to 0° C. A solution of 193.75 g (1.25 mol) of γ-chloroacetoacetyl chloride (γ-CAC) in 431 ml of methylene chloride is added at the same temperature over an hour and, after completion of the addition, the mixture is stirred for 30 minutes. The resulting pyridine hydrochloride is filtered off. The filtrate and washings are combined and washed with 2 l-portions of water. The organic layer is dried over sodium sulfate and the solvent is then distilled off to give 354 g of p-nitrobenzyl γ-chloroacetoacetate as an oil.

Workup

  1. temperaturethe mixture is cooled to -5° to 0° C
  2. additionafter completion of the addition
  3. filtrationThe resulting pyridine hydrochloride is filtered off
  4. washwashed with 2 l-portions of water
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. distillationthe solvent is then distilled off

Sources & evidence

ORD record
ord-bd0e50e137d3417da7d549a5d1eba38e
Source dataset
uspto-grants-1986_02
Patent number
US04572801

Linked notes

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