Acetic Anhydride → HCID 537346, compound

HRID 1650930Notes

Reaction equation

HRID 1650930 reaction equation
[CH3:1][CH:2]([CH2:7][CH:8]([CH3:13])[CH:9]([OH:12])[CH2:10][CH3:11])[C:3](=[O:6])[CH2:4][CH3:5].[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[CH3:1][CH:2]([CH2:7][CH:8]([CH3:13])[CH:9]([O:12][C:14](=[O:16])[CH3:15])[CH2:10][CH3:11])[C:3](=[O:6])[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 1944547-Hydroxy-4,6-dimethyl-3-nonanone

Product 1

HCID 537346HCID 537346, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 4,6-dimethyl-7-hydroxynonan-3-one (IVa, 10 g, 53.8 mmoles) in acetic anhydride (13.8 g, 135 mmoles) and pyridine (12.8 g, 162 mmoles) was set stirring under a nitrogen atmosphere. After stirring for 20 hours at room temperature, most of the acetic anhydride and pyridine were removed at reduced pressure to leave a clear oil (11 g crude weight). The crude product was then distilled at 60° C. and 0.16 mm to give a 68% yield of 4,6-dimethyl-7-acetoxynonan-3-one (8.4 g, 36.8 mmoles).

Workup

  1. customwere removed at reduced pressure
  2. customto leave a clear oil (11 g crude weight)
  3. distillationThe crude product was then distilled at 60° C.

Sources & evidence

ORD record
ord-185767fe66b849338c52bd64618b7dce
Source dataset
uspto-grants-1990_05
Patent number
US04925985

Reaction notes

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