Benzyl Alcohol → benzyl chlorooxalate

HRID 1608308Notes

Reaction equation

HRID 1608308 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[CH2:7]([O:14][C:1](=[O:5])[C:2]([Cl:4])=[O:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 65578Oxalyl chloride

Product 1

HCID 11019858benzyl chlorooxalateYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under N2, oxalyl chloride (262 ml) was dissolved in 1 liter anhydrous ether and heated to reflux, at which temperature benzyl alcohol (207 ml) was added over 70 minutes. After refluxing a further 16 hours, ether was stripped and the residue distilled at reduced pressure to yield 372 g (94%) of title product, b.p./0.7 mm 85° C.

Workup

  1. temperatureheated
  2. additionwas added over 70 minutes
  3. temperatureAfter refluxing a further 16 hours
  4. distillationthe residue distilled at reduced pressure

Sources & evidence

ORD record
ord-17cab14942c14f2f8abb9d25ceea1341
Source dataset
uspto-grants-1989_09
Patent number
US04870170

Reaction notes

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