Sodium Carbonate → 2-Ethylhexanoylmethylenetriphenylphosphorane

HRID 1581112Notes

Reaction equation

HRID 1581112 reaction equation
[Cl-].[O:2]=[C:3]([CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:4][P+:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:29]([CH:24]([CH2:25][CH2:26][CH2:27][CH3:28])[C:3]([CH:4]=[P:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:2])[CH3:30]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 215614842-Oxo-3-ethylheptyltriphenylphosphonium chloride

Product 1

HCID 215614912-Ethylhexanoylmethylenetriphenylphosphorane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Crude 2-oxo-3-ethylheptyltriphenylphosphonium chloride (88 g.) was added to a solution of sodium carbonate (100 g.) in water (1 litre) and the mixture stirred vigorously for 24 hours. The mixture was then extracted with diethyl ether and the extracts dried over magnesium sulphate. The solvent was evaporated and the crude product (63.3 g.) recrystallised from petrol (b.p. 60°-80°C.) to give 2-ethylhexanoylmethylenetriphenylphosphorane, m.p. 105.5°-107.5°C. (Found: C, 80.2; H, 7.5. C27H31OP requires C, 80.5; H, 7.5%).

Workup

  1. extractionThe mixture was then extracted with diethyl ether
  2. dry with materialthe extracts dried over magnesium sulphate
  3. customThe solvent was evaporated
  4. customthe crude product (63.3 g.) recrystallised from petrol (b.p. 60°-80°C.)

Sources & evidence

ORD record
ord-caecd330994142eb9376a3d1011e8b56
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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