Methyl hexanoate → HCID 53695514, compound

HRID 1277744Notes

Reaction equation

HRID 1277744 reaction equation
C(OC)(=O)CCCCC.C[O-].[Na+].[C]=O.[CH3:15][O:16][C:17](=[O:25])[CH:18]([CH:23]=[O:24])[CH2:19][CH2:20][CH2:21][CH3:22].[Cl:26][CH2:27][CH2:28][CH2:29][CH2:30]Br>CC(N(C)C)=O.CO>[CH3:15][O:16][C:17](=[O:25])[C:18]([CH2:19][CH2:20][CH2:21][CH3:22])=[CH:23][O:24][CH2:30][CH2:29][CH2:28][CH2:27][Cl:26]

Participants

8

Reactant 5

HCID 7824Methyl hexanoateHCID 813641-Bromo-4-chlorobutaneHCID 10942334Sodium MethoxideHCID 19862278Methyl 2-formylhexanoateHCID 178418416HCID 178418416, compound

Product 1

HCID 53695514HCID 53695514, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

162.5 g Methyl caproate (1.25 mole), 28 g 96% sodium methylate (0.5 mole), and 10 ml methanol were reacted with carbon monoxide in the manner described in Example 4, and approximately 100 g crude sodium enolate of 2-formylcaproic acid methyl ester was obtained as an evaporation residue. It was suspended in 180 ml dimethylacetamide and mixed with 103 g 4-chlorobutyl bromide. The mixture was stirred about 4-6 hours at 65°-70° C., and worked up in a manner analogous to the procedure of Example 5. 74.5 g 3-(4-chlorobutoxy)-2-butyl-acrylic acid methyl ester boiling at 155° C./2 torr was obtained for a 60% yield based on the sodium methylate employed.

Workup

  1. customwas obtained as an evaporation residue

Sources & evidence

ORD record
ord-d4b25d805f554a5ca240cd74bb1775b5
Source dataset
uspto-grants-1981_07
Patent number
US04278808

Reaction notes

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