Acetic Anhydride → 12-Acetoxy-15-pentadecanolide

HRID 1109255Notes

Reaction equation

HRID 1109255 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OC1[CH2:25][CH2:24][CH2:23][O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]C1>>[C:5]([O:4][CH:1]1[CH2:25][CH2:24][CH2:23][O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:2]1)(=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 309431913-Hydroxy-oxacyclohexadecan-2-one

Product 1

HCID 1504169212-Acetoxy-15-pentadecanolideYield 98%

Procedure

473 g (4.64 mol) of acetic anhydride are initially introduced into a flask and heated to 135°-140° C. (reflux). 982 g (3.83 mol) of 12-hydroxy-15-pentadecanolide (VII) are added dropwise. The mixture is allowed to after-react under reflux for a further hour. The excess acetic acid/acetic anhydride is then distilled off under a weak vacuum. 1120 g of 12-acetoxy-15-pentadecanolide are obtained;

Workup

  1. temperatureheated to 135°-140° C.
  2. temperature(reflux)
  3. customto after-react
  4. temperatureunder reflux for a further hour
  5. distillationThe excess acetic acid/acetic anhydride is then distilled off under a weak vacuum

Sources & evidence

ORD record
ord-b18b715a3d934fccbad4aa37a47d74b1
Source dataset
uspto-grants-1994_06
Patent number
US05319104

Reaction notes

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