Thionyl Chloride → Methyl 13-chloro-13-oxotridecanoate

HRID 569110Notes

Reaction equation

HRID 569110 reaction equation
[CH2:1]([C:15]([O:17][CH3:18])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O-])=[O:13].O=S(Cl)[Cl:21]>C(Cl)Cl>[CH3:18][O:17][C:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([Cl:21])=[O:13])=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2293981513-Methoxy-13-oxotridecanoate

Product 1

HCID 12956021Methyl 13-chloro-13-oxotridecanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution of 4.8 gms monomethyl 1,11-undecanedicarboxylate in 10 ml CH2Cl2 was added 5 ml SOCl2 dropwise over 5 minutes; then it was stirred at room temperature for 18 hours. The solvent was removed in vacuo to give 4.8 gms of an oily residue which was used without further purification.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8a1d02c9f96e453f9045581713e4f808
Source dataset
uspto-grants-1988_03
Patent number
US04731382

Reaction notes

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