12-Hydroxystearic acid → 12-Hydroxyoctadecane-1,12-lactone

HRID 2419222Notes

Reaction equation

HRID 2419222 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[OH:10][CH:11]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23].C(N(CC)CC)C>C(#N)C>[OH:10][C:11]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 778912-Hydroxystearic acidHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 8673588412-Hydroxyoctadecane-1,12-lactoneYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a refluxing solution of 510 mg (2.0 mmol) of 2-chloro-1-methylpyridinium iodide in 50 ml of acetonitrile, there was added a solution of 150 mg (0.5 mmol) of 12-hydroxyoctadecanoic acid and 404 mg (4.0 mmol) of triethylamine in 40 ml of acetonitrile over a period of 8 hours at a continuous and uniform rate, and the reaction mixture was refluxed for an additional 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 12-hydroxyoctadecane-1,12-lactone was obtained in 66% yield.

Workup

  1. temperaturethe reaction mixture was refluxed for an additional 30 minutes
  2. additionafter the addition
  3. customAfter evaporation of the solvent
  4. customthe residue was separated chromatographically on a silica gel column

Sources & evidence

ORD record
ord-76e97f1c0e454fa9bb83bea21dfdaaf1
Source dataset
uspto-grants-1978_08
Patent number
US04105673

Reaction notes

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