2-Undecanone → HCID 76463741, compound

HRID 2308396Notes

Reaction equation

HRID 2308396 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(OP([CH2:21][C:22]([O:24][CH3:25])=[O:23])(OCC)=O)C.C[O-].[Na+]>C1C=CC=CC=1.CO>[CH3:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH:21][C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 81632-UndecanoneHCID 66113Methyl diethylphosphonoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 76463741HCID 76463741, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

2-Undecanone (methyl nonyl ketone) (1′) (73.9 g, 434 mmols) and methyl (diethylphosphono)acetate (99.4 g, 433 mmols) were dissolved in dry benzene (300 ml). The solution was stirred at room temperature, and a 28% sodium methoxide solution (83.7 g) in methanol was slowly added. Stirring was continued overnight at room temperature. The reaction mixture was poured into ice water, and extracted with diethyl ether. The organic layer was washed (water and a saturated aqueous solution of sodium chloride), and dried (sodium sulfate), followed by removing the solvent in a vacuum to obtain methyl 3-methyl-2-dodecenoate (2′) as a geometric isomer mixture.

Workup

  1. stirringStirring
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed (water
  4. dry with materiala saturated aqueous solution of sodium chloride), and dried (sodium sulfate)
  5. customby removing the solvent in a vacuum

Sources & evidence

ORD record
ord-3392fcbe79c3462186fa0de6ecc9028b
Source dataset
uspto-grants-2004_12
Patent number
US06835846B2

Reaction notes

Loading…