Phosphorus oxide (P4O10) → 1-(5,5-Dimethylcyclohex-1-en-1-yl)ethan-1-one

HRID 746365Notes

Reaction equation

HRID 746365 reaction equation
[O:1]=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]([C:17]1(O)[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[CH2:18]1)#[CH:16]>CC1C=CC=CC=1>[CH3:16][C:15]([C:17]1[CH2:18][C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][CH:22]=1)=[O:1]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 2056939157559-98-5

Product 1

HCID 126685191-(5,5-Dimethylcyclohex-1-en-1-yl)ethan-1-oneYield 38.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus pentoxide (33.1 g, 233 mmol) was added to a solution of 1-ethynyl-3,3-dimethylcyclohexanol (152 g, 1.00 mol) in MePh (800 ml). The slurry was heated to reflux, and stirred at this temp. for 90 min. The reaction mixture was allowed to cool to room temp., and then poured into ice/water (1:1, 500 ml). The product was extracted with Et2O (2×500 ml), and the combined organic extracts were washed with water (500 ml) and brine (100 ml), dried (Na2SO4) and concentrated under reduced pressure. Silica-gel FC (pentane/Et2O, 9:1, Rf=0.70) provided 13.8 g (9%) of 1-(5′,5′-dimethylcyclohex-1′-enyl)ethanone.

Workup

  1. temperatureThe slurry was heated
  2. temperatureto reflux
  3. temperatureto cool to room temp.
  4. extractionThe product was extracted with Et2O (2×500 ml)
  5. washthe combined organic extracts were washed with water (500 ml) and brine (100 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11a789913357453aaf7eda714606a49f
Source dataset
uspto-grants-2008_07
Patent number
US07393822B2

Reaction notes

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