Oxalyl chloride → HCID 11041567, compound

HRID 2352647Notes

Reaction equation

HRID 2352647 reaction equation
[CH3:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O>C1C=CC=CC=1>[CH3:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4]([Cl:16])=[O:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 13191833(R)-(+)-3,7-dimethyloctanoic acid

Product 1

HCID 11041567HCID 11041567, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 11.37 g (66.1 mmoles) of (R)-(+)-3,7-dimethyloctanoic acid in 50 ml of benzene was stirred while 10 ml (114.6 mmoles) of oxalyl chloride was added. The solution was stirred and refluxed overnight then concentrated in vacuo giving 12.03 g (95.6%) of (R)-(+)-3,7-dimethyloctanoyl chloride as an oil. An 8.2 g (43.0 mmoles) sample of this material in 10 ml of dichloromethane was added to a stirred solution of 6.2 (43.0 mmoles) of Meldrum's Acid and 8.68 ml of pyridine in 40 ml of dichloromethane, at 0° C. The resulting solution was stirred overnight then treated with cold 3N aqueous HCl. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The dichloromethane extracts were combined, dried (Na2SO4), and concentrated in vacuo giving 12.1 g of crude product. This material was dissolved in 100 ml of methanol and the solution was refluxed for 4 hr then cooled and concentrated in vacuo. The residue was chromatographed on silica gel giving (R)-5,9-dimethyl-3-oxodecanoic acid methyl ester as an oil, eluted with pet. ether-ether mixtures.

Workup

  1. additionwas added
  2. temperaturerefluxed overnight
  3. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-5e3b6803a501460bb9d7678c1d5cb94d
Source dataset
uspto-grants-1989_10
Patent number
US04877890

Reaction notes

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