Mesityl oxide → Piperitenone

HRID 1251624Notes

Reaction equation

HRID 1251624 reaction equation
[O:1]=[C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])[CH3:3].[OH-].[CH2:9]([N+](C)(C)C)[C:10]1C=CC=C[CH:11]=1.O[CH2:21]CC(=O)C>C(O)(=O)C>[CH3:6][C:5]1[CH2:7][CH2:21][C:3](=[C:10]([CH3:11])[CH3:9])[C:2](=[O:1])[CH:4]=1

Participants

5

Reactant 3

HCID 8858Mesityl oxideHCID 66854Benzyltrimethylammonium hydroxideHCID 1115094-Hydroxy-2-Butanone

Product 1

HCID 381152PiperitenoneYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A 688 ml (6.0 mol) portion of mesityl oxide was put into a one liter capacity four neck flask, 4.18 ml (10 mmol) of 40% benzyltrimethylammonium hydroxide aqueous solution was added dropwise thereto and the mixture was heated to 80° C. To this was added dropwise 172 ml (2.0 mol) of 4-hydroxy-2-butanone spending 1 hour while keeping at 80° C. After completion of the dropwise addition, this was stirred for 30 minutes and then neutralized by adding dropwise 0.69 ml of acetic acid. By carrying out distillation of the reaction solution under a reduced pressure, 180 g of piperitenone was obtained. Yield 60%.

Workup

  1. additionwas added dropwise
  2. customwhile keeping at 80° C
  3. additionAfter completion of the dropwise addition
  4. distillationdistillation of the reaction solution under a reduced pressure

Sources & evidence

ORD record
ord-83d1826d5c254b6890b0878c2d831240
Source dataset
uspto-grants-2002_01
Patent number
US06342644B1

Reaction notes

Loading…