Hexanoyl chloride → Methyl-5-oxo-decenoate

HRID 268102Notes

Reaction equation

HRID 268102 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:13]([O:18][CH3:19])(=[O:17])/[CH:14]=[CH:15]/[CH3:16]>ClC(Cl)C>[CH3:19][O:18][C:13](=[O:17])[CH:14]=[CH:15][CH2:16][C:5](=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 67340Hexanoyl chlorideHCID 638132Methyl CrotonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 166281Methyl-5-oxo-decenoate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 26.5 g (0.2 moles) of aluminum chloride in 50 cc of dichloroethane is added a solution of 13.5 g (0.1 moles) of hexanoyl chloride and 10.0 g (0.1 moles) of methyl crotonate. Over a period of 10 minutes the temperature rises from 25 to 60°C. The reaction mass is refluxed for 4 hours at a temperature of approximately 90°C. The resultant methyl-5-oxo-decenoate is formed only in a small amount (approximately 2-3%).

Sources & evidence

ORD record
ord-1977b0c337cf49cdb73fec2bf7ff7121
Source dataset
uspto-grants-1976_03
Patent number
US03946054

Reaction notes

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