Phosphorus pentachloride → Nervonoyl chloride

HRID 432971Notes

Reaction equation

HRID 432971 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]([OH:32])(=O)[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]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(OCC)C>[C:7]([Cl:2])(=[O:32])[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]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 5281120Nervonic Acid

Product 1

HCID 11199988Nervonoyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosphorus pentachloride (0.123 mol, 25.6 g) was added gradually to a solution of nervonic acid (available from Aldrich Chemicals) (0.123 mol, 45.0 g) in dry ethyl ether (225 mL, C=200 g.L−1). The mixture was stirred at room temperature under nitrogen for 3 h and concentrated to dryness to yield z-15-tetracosenoyl chloride as pale yellow, fairly viscous oil.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6eac6a23586a48b381e7d8fd2a6f80fd
Source dataset
uspto-grants-2003_12
Patent number
US06664406B1

Reaction notes

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