Oxalyl chloride → HCID 67481270, compound

HRID 495344Notes

Reaction equation

HRID 495344 reaction equation
[C:1]([O:12][CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([O-])=[O:5].C(Cl)(=O)C(Cl)=O>>[OH:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([O:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH3:18])=[O:11]

Participants

3

Reactant 2

HCID 65578Oxalyl chlorideHCID 86584594HCID 86584594, compound

Product 1

HCID 67481270HCID 67481270, compoundYield 31.8%

Procedure

1 g (4.03 mmol) monohexenyl phthalate was heated at reflux in 6 ml oxalyl chloride (17.3 eq.) for 1.5 h. The excess oxalyl chloride was distilled under vacuum. The crude acid chloride was then diluted in 10 ml dichloromethane cooled to 0° under argon, and introduced dropwise on a solution of 2.07 g (2 eq.) nBuNBH4 in 10 ml dichloromethane. The reaction mixture was maintained under stirring at 0° for 2.5 h. The mixture was then poured over 5% KHSO4 and cold ethyl ethyl acetate, and extracted. Chromatography of the crude product over silica gel (85:15 cyclohexane/AcOEt) yielded 0.3 g (32%) (Z)-3-hexenyl 2-hydroxymethylbenzoate containing about 10% phthalide, in the form of a colourless oil.

Workup

  1. distillationThe excess oxalyl chloride was distilled under vacuum
  2. additionThe crude acid chloride was then diluted in 10 ml dichloromethane
  3. temperaturecooled to 0° under argon
  4. additionintroduced dropwise on a solution of 2.07 g (2 eq.)
  5. temperatureThe reaction mixture was maintained
  6. additionThe mixture was then poured over 5% KHSO4 and cold ethyl ethyl acetate
  7. extractionextracted

Sources & evidence

ORD record
ord-276c625f7f224a8c9fd1e1a8013359e0
Source dataset
uspto-grants-2005_09
Patent number
US06939835B2

Reaction notes

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