Tetrahydrofuran → Benzoyloxymethyl chloroformate

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

Reactant 3

HCID 8028Tetrahydrofuran

HCID 65578Oxalyl chloride

HCID 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.