Sodium Hydroxide → Phenoxyacetylmethylenetriphenylphosphorane

HRID 893894Notes

Reaction equation

HRID 893894 reaction equation
[Cl-].[O:2]([CH2:9][C:10]([CH2:12][P+:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>O>[O:2]([CH2:9][C:10]([CH:12]=[P:13]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20516787Phenoxyacetylmethyltriphenylphosphonium Chloride

Product 1

HCID 11015099Phenoxyacetylmethylenetriphenylphosphorane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenoxyacetylmethyltriphenylphosphonium chloride (10 g, 22.40 mmol) was suspended in 250 ml water with a few crystals of phenolphthalien added as an indicator. Sodium hydroxide (5%) was added dropwise until the vigorously stirred mixture turned pink. The white solid was collected, washed with water, and dried in a desicator, weight 9 g (98%); mp 127-128.5; ir (KBr, cm-1) 1595, 1580, 1540, 1480, 1435, 1400, 1225, 1105, 1045, 870; nmr (DCCl3, ppm) 7.90-6.90 (m, 21H), 4.53 (s, 2H).

Workup

  1. additionadded as an indicator
  2. customThe white solid was collected
  3. washwashed with water
  4. customdried in a desicator, weight 9 g (98%)

Sources & evidence

ORD record
ord-c392b28df73c44a98ce651242f37ba1b
Source dataset
uspto-grants-1981_08
Patent number
US04282149

Reaction notes

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