Acetic Anhydride → HCID 11041076, compound

HRID 1779707Notes

Reaction equation

HRID 1779707 reaction equation
[CH3:1][CH:2]([C:7](=[O:13])[CH2:8][CH2:9][C:10]([CH3:12])=[CH2:11])[CH2:3][C:4]([OH:6])=O.C(OC(=O)C)(=O)C>>[CH3:1][C:2]1[CH:7]([CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12])[O:13][C:4](=[O:6])[CH:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 110195357-Octenoic acid, 3,7-dimethyl-4-oxo-

Product 1

HCID 11041076HCID 11041076, compound

Procedure

The thus-obtained 3,7-dimethyl-4-oxo-7-octenoic acid is then dissolved in a solvent and an equivalent amount or a somewhat excessive amount of acetic anhydride is added thereto and heated under reflux in the presence of an acid catalyst, whereby the acid is cyclized and dehydrated along with isomerization of the terminal double bond to give 3,7-dimethyl-2,6-octadien-4-olide. As the solvent in this process, usable is a hydrocarbon solvent such as pentane, hexane, heptane, benzene, toluene, xylene or the like. Especially preferred is toluene. As the acid catalyst, usable is an organic acid such as acetic acid, para-toluene-sulfonic acid, camphor-sulfonic acid or the like.

Workup

  1. temperatureheated
  2. temperatureunder reflux in the presence of an acid catalyst, whereby the acid

Sources & evidence

ORD record
ord-252282c9a713493783db2779cb37c19f
Source dataset
uspto-grants-1997_05
Patent number
US05627288

Reaction notes

Loading…