Tetrahydrofuran → Benzoyloxymethyl chloroformate

HRID 1488886Notes

Reaction equation

HRID 1488886 reaction equation
[C:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]CCCCCCCCC(O)=O)(=[O:17])CCCCCCCCCCCCCCC.C(Cl)(=O)[C:38]([Cl:40])=[O:39].[O:43]1CCCC1>>[Cl:40][C:38]([O:17][CH2:1][O:18][C:19](=[O:43])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:39]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 1960674616-Hexadecanoyloxyhexadecanoic acid

Product 1

HCID 14800986Benzoyloxymethyl chloroformateYield 100%

Procedure

16-Hexadecanoyloxyhexadecanoic acid (7.73 g, 15.13 mmol) prepared as in (ah) above was dissolved in tetrahydrofuran (140 ml) and oxalyl chloride (4.80 g, 37.83 mmol) was added dropwise. The mixture was stirred at room temperature for 3 days and then the solvent and unreacted oxalyl chloride were evaporated under reduced pressure to give 8.0 g (100%) of the title compound.

Workup

  1. customthe solvent and unreacted oxalyl chloride were evaporated under reduced pressure

Sources & evidence

ORD record
ord-921ef381772b40d19bbfa3d65b4afb8e
Source dataset
uspto-grants-1997_10
Patent number
US05676925

Reaction notes

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