Benzyl Chloride → Benzyl 4-methyl-2-oxopentanoate

HRID 326377

Reaction equation

HRID 326377 reaction equation
[Na+].[O:2]=[C:3]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O-:6])=[O:5].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:9][CH:8]([CH3:10])[CH2:7][C:3](=[O:2])[C:4]([O:6][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5]

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 4137900Sodium 4-methyl-2-oxovalerate

Product 1

HCID 4072499Benzyl 4-methyl-2-oxopentanoateYield 94%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-Oxo-4-methyl pentanoic acid sodium salt (10 g, 65.7 mmol) and benzyl chloride (8 g, 63 mmol) in 300 ml DMF was stirred at 40°-50° C. for 5 h. It was filtered, and the filtrate was evaporated under reduced pressure to provide an oil. The oil was dissolved in chloroform, washed with water, dried, filtered, and evaporated to provide the desired product (13 g, 94%). 1H NMR (CDCl3, TMS) δ0.95 (d,6H), 2.15 (m,1H), 2.7 (d,2H), 5.28 (s,2H), 7.4 (m,5H). Mass spectrum: (M+H)+ =221.

Workup

  1. filtrationIt was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customto provide an oil
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-17556ae88132457880ffb3476e669674
Source dataset
uspto-grants-1993_12
Patent number
US05268374

Linked notes

Loading…