Undecylenic Acid → 10-Undecenoyl chloride

HRID 2193830Notes

Reaction equation

HRID 2193830 reaction equation
O=S(Cl)[Cl:3].[C:5]([OH:17])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15]>C1(C)C=CC=CC=1>[C:5]([Cl:3])(=[O:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 5634Undecylenic AcidHCID 24386Thionyl Chloride2×

Product 1

HCID 3804210-Undecenoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of toluene (12 mL) and SOCl2 (7.75 g, 65 mmol) and undec-10-enoic acid (1.00 g, 5.43 mmol) were refluxed for 1.5 h. The solvent and remaining SOCl2 were distilled off and the product (X) was further used in the thioester synthesis. 1H-NMR (CDCl3): δ=5.90-5.74 (m, 1H), 5.06-4.91 (m, 2H), 2.87 (t, J=7.2 Hz, 2H), 2.06 (q, J=13.7 Hz, J=6.7 Hz, 2H), 1.78-1.61 (m, 2H), 1.49-1.23 (m, 8H).

Workup

  1. temperaturewere refluxed for 1.5 h
  2. distillationwere distilled off
  3. customthe product (X) was further used in the thioester synthesis

Sources & evidence

ORD record
ord-da23d6af23f9447cb03214025fa33c33
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

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