Acetic Anhydride → 3,5-Dioxohexanoic acid

HRID 1610039Notes

Reaction equation

HRID 1610039 reaction equation
OCCCN[C:6](=O)[C@H:7]([C:9]([CH2:12][OH:13])(C)C)[OH:8].CN(C1C=CC=CN=1)C.C([O:27][C:28](=[O:30])[CH3:29])(=O)C>>[CH3:6][C:7]([CH2:9][C:12]([CH2:29][C:28]([OH:27])=[O:30])=[O:13])=[O:8]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 5748487L-Panthenol

Product 1

HCID 54598443,5-Dioxohexanoic acid

Conditions

Temperature
80 °C

Procedure

D-panthenol (88 grams, 0.424 moles) and polymer bound dimethylaminopyridine (2 grams) were added to a flask. Acetic anhydride (144.4 grams, 3.3 moles) was slowly added to the stirring mixture, and the resultant exotherm was controlled when the temperature reached 80° C. The mixture was heated at 80° C. and stirred for 9 hours. The flask was then fitted for vacuum distillation, and the acetic acid was removed under reduced pressure to a concentration of about 4% w/w. The catalyst (P-DMAP) was filtered out from the reaction mixture. The solution was treated with a 50% w/w solution of sodium hydroxide in a volume sufficient to neutralize the residual acetic acid, and the resultant solids of sodium acetate were removed by filtration. The residual water was then removed under vacuum to afford about 80% of the desired product, D-panthenyl triacetate.

Workup

  1. customreached 80° C
  2. customThe flask was then fitted for vacuum distillation
  3. customthe acetic acid was removed under reduced pressure to a concentration of about 4% w/w
  4. filtrationThe catalyst (P-DMAP) was filtered out from the reaction mixture
  5. additionThe solution was treated with a 50% w/w solution of sodium hydroxide in a volume sufficient
  6. customthe resultant solids of sodium acetate were removed by filtration
  7. customThe residual water was then removed under vacuum

Sources & evidence

ORD record
ord-9850ad8f052c496989bab0437873a495
Source dataset
uspto-grants-2006_01
Patent number
US06982346B2

Reaction notes

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