Undecylenic Acid → 10-Undecenoyl chloride

HRID 1781967Notes

Reaction equation

HRID 1781967 reaction equation
[C:1]([OH:13])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C(Cl)(C([Cl:18])=O)=O>C(Cl)Cl>[C:1]([Cl:18])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 5634Undecylenic AcidHCID 65578Oxalyl chloride

Product 1

HCID 3804210-Undecenoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 10-undecenoic acid (5.055 mL, 25 mmol) in CH2Cl2 (50 mL) was slowly added (COCl)2 (4.364 mL, 50 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure to give 10-undecenoyl chloride (25 mmol). The product was used for the next reaction without further purification. 1H NMR (500 MHz, CDCl3) δ 1.29-1.48 (m, 10H), 1.71 (m, 2H), 2.05 (m, 2H), 2.88 (t, J=7 Hz, 2H), 4.98 (m, 2H), 5.80 (m, 1H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f4736c1983ad4437920881e9356b17a0
Source dataset
uspto-grants-2009_03
Patent number
US07498292B2

Reaction notes

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