Thionyl Chloride → Methyl 13-chloro-13-oxotridecanoate

HRID 1723403Notes

Reaction equation

HRID 1723403 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-a3b8a410019249238590f91b3d9c5280
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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