Acetic Acid → HCID 178439162, compound

HRID 382923

Reaction equation

HRID 382923 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[C:5](O)([CH3:8])([CH3:7])[CH3:6].O.[CH2:11]=[C:12]=[O:13].[CH2:14](N(CC)CC)[CH3:15]>>[CH3:6][CH:5]([C:8]1[CH:2]=[C:1]([OH:4])[C:12](=[O:13])[CH:11]=[CH:15][CH:14]=1)[CH3:7]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 6386tert-ButanolHCID 8471TriethylamineHCID 10038Ketene2×

Product 1

HCID 178439162HCID 178439162, compoundYield 66%

Conditions

Temperature
60 °C

Procedure

A mixed solvent consisting of 24 g of acetic acid, 377 g of t-butanol and 49 g of water was added to the distillate containing the ketene adducts, and 99 g of triethylamine was added dropwise over a period of 2 hours while maintaining the solution temperature at 60° C. Then, the resulting mixture was heated at 60° C. for another 5 hours. After completion of the reaction, analysis by a gas chromatography revealed that peaks due to the ketene adducts disappeared and that hinokitiol was obtained in 66% yield (0.26 mol).

Workup

  1. additionwas added to the distillate
  2. additionwas added dropwise over a period of 2 hours
  3. temperatureThen, the resulting mixture was heated at 60° C. for another 5 hours
  4. customAfter completion of the reaction, analysis by a gas chromatography

Sources & evidence

ORD record
ord-140131d9b60e4aab9f931625c05db0da
Source dataset
uspto-grants-2001_10
Patent number
US06310255B1

Linked notes

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