Pyridine → 3-Chlorocarbonyl-propionic acid 3,7-dimethyl-oct-6-enylester

HRID 1533697Notes

Reaction equation

HRID 1533697 reaction equation
[CH3:1][CH:2]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH2:3][CH2:4][O:5][C:6](=[O:12])[CH2:7][CH2:8][C:9](O)=[O:10].N1C=CC=CC=1.S(Cl)([Cl:27])=O>CCOCC>[CH3:1][CH:2]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH2:3][CH2:4][O:5][C:6](=[O:12])[CH2:7][CH2:8][C:9]([Cl:27])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 111728904-[(3,7-Dimethyloct-6-en-1-yl)oxy]-4-oxobutanoic acid

Product 1

HCID 153907233-Chlorocarbonyl-propionic acid 3,7-dimethyl-oct-6-enylesterYield 82.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 35.5 g succinic acid mono-(3,7-dimethyl-oct-6-enyl) ester and 12.3 g pyridine in 200 ml of ether was cooled in an ice bath. Then a solution of 18.0 g thionyl chloride in 100 ml of ether was added dropwise at 5-10° C. during 90 min. The resulting solution was stirred overnight at room temperature, then it was filtered and evaporated to dryness. The residue was not further purified to yield 31.5 g of a yellow liquid.

Workup

  1. filtrationit was filtered
  2. customevaporated to dryness
  3. customThe residue was not further purified

Sources & evidence

ORD record
ord-770b23c73dbf47c094c8bccfe31f4038
Source dataset
uspto-grants-2001_03
Patent number
US06207857B1

Reaction notes

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