Thionyl Chloride → Methyl 21-chloroformylheneicosanoate

HRID 1903420Notes

Reaction equation

HRID 1903420 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)=[O:4].S(Cl)([Cl:30])=O>>[Cl:30][C:25]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:27]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 34736122-Methoxy-22-oxodocosanoic acid

Product 1

HCID 20431167Methyl 21-chloroformylheneicosanoate

Procedure

One gram of 1,20-eicosanedicarboxylic acid monomethyl ester is dissolved in 5 ml of thionyl chloride. After stirring at room temperature for 12 hours, excess thionyl chloride is distilled off under reduced pressure to give crude crystals of methyl 21-chloroformylheneicosanoate. This product is submitted to the following step without purification.

Workup

  1. distillationexcess thionyl chloride is distilled off under reduced pressure

Sources & evidence

ORD record
ord-9848f02cdc4c4fd6bc52b4ab08243eac
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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