Stearic Acid → Stearoyl chloride

HRID 217544Notes

Reaction equation

HRID 217544 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7](O)(=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][CH2:21][CH2:22]CC>C(Cl)(Cl)Cl>[C:2]([Cl:4])(=[O:3])[CH2:1][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Participants

4

Reactant 2

HCID 5281Stearic AcidHCID 65578Oxalyl chloride

Product 1

HCID 8212Stearoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of oxalyl chloride (53.5 g, 422 mmol) in 150 mL of chloroform was added drop wise to a solution of stearic acid (30.0 g, 105 mmol) in 250 mL of chloroform. After stirring overnight at ambient temperature the solution was concentrated and co-evaporated twice with chloroform. Drying under vacuum for 1 hour yielded a quantitative yield of a white solid. 1H-NMR (CDCl3): δ=2.85 (t, 2H), 1.70 (q, 2H), 1.30 (m, 28H), 0.85 (t, 3H) ppm. 13C-NMR (CDCl3): δ=173.6, 47.1, 31.9, 29.7, 29.7, 29.6, 29.5, 29.4, 29.3, 29.1, 28.4, 25.1, 22.7, 14.1 ppm. FT-IR: ν=2292, 2853, 1799 (C═O stretch), 1466, 953, 720, 680 cm−1.

Workup

  1. concentrationwas concentrated and co-evaporated twice with chloroform
  2. customDrying under vacuum for 1 hour

Sources & evidence

ORD record
ord-89d55cccb7424fba861bef960628c3e6
Source dataset
uspto-grants-2012_06
Patent number
US08197589B2

Reaction notes

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