Tributylamine → Pentadecalactone

HRID 2419219Notes

Reaction equation

HRID 2419219 reaction equation
[I-].ClC1C=CC=C[N+]=1C.O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26].C(N(CCCC)CCCC)CCC>C(#N)C>[CH2:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:26])[O:27][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 7836015-Hydroxypentadecanoic acidHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 235414PentadecalactoneYield 74%

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 134 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 740 mg (4.0 mmol) of tri-n-butylamine 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. 1,15-pentadecanolide was obtained in 74% 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-9465150e2a78425bb191302950f0740c
Source dataset
uspto-grants-1978_08
Patent number
US04105673

Reaction notes

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