Potassium Bicarbonate → 15-(Dimethylphosphono)-pentadec-12-en-14-on-1-al

HRID 67270Notes

Reaction equation

HRID 67270 reaction equation
C(=O)(O)[O-].[K+].COP([CH2:12][C:13](=[O:21])[CH2:14][P:15]([O:19][CH3:20])([O:17][CH3:18])=[O:16])(OC)=O.[CH:22](=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[O:34]>O.C(O)(C)(C)C>[CH3:20][O:19][P:15]([CH2:14][C:13](=[O:21])[CH:12]=[CH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[O:34])([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 5743459DodecanedialHCID 135122551,3-Bis(dimethylphosphono)propan-2-one

Product 1

HCID 5421448415-(Dimethylphosphono)-pentadec-12-en-14-on-1-al

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 5 g of potassium bicarbonate in 150 ml of water was added to a mixture of 8.22 g (30 mMole) of 1,3-bis(dimethylphosphono)propan-2-one and 5.94 g (80 mMole) of dodecan-1,12-dial in 150 ml of t-butanol. After 21/2 h stirring at 27° under nitrogen water was added and the mixture was extracted with ether. The organic layer was separated, washed with brine, dried over sodium sulphate and evaporated. The residue was chromatographed on 150 g of silica gel. Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residue was chromatographed on 150 g of silica gel
  8. washHexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether
  9. washeluted
  10. custom4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil

Sources & evidence

ORD record
ord-9ee70a8dc72b4b64b9639cac114da397
Source dataset
uspto-grants-1982_08
Patent number
US04346023

Reaction notes

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