Water → HCID 178520471, compound

HRID 1288219Notes

Reaction equation

HRID 1288219 reaction equation
[Cl-].[O:2]=[C:3]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[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.O>[OH-].[Na+]>[O:2]=[C:3]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[CH2:4][PH:5]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 962WaterHCID 21503863HCID 21503863, compound

Product 1

HCID 178520471HCID 178520471, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 29.25 g. of (2-oxo-4-p-fluorophenylbutyl)-triphenylphosphonium chloride of part 3, in 250 ml. of warm water is added 80 ml. of IN sodium hydroxide solution. An oil separates which solidifies. The solid is collected by filtration and dissolved in methylene chloride. The solution is dried and then concentrated on a steam bath. Skellysolve B is added to the boiling solution. Cooling gives cream prisms of the title compound (25.85 g.); m.p. 123°-125°. The infrared spectrum shows absorptions at 3490, 3540, 3240, 1605, 1590, 1575, 1550, 1525, 1510, 1485, 1440, 1390, 1220, 1105, 875, 860, 755, 720, and 700 cm -1. NMR peaks are observed at 2.6-3.0, 6.9-7.4 and 7.4-7.8 δ.

Workup

  1. filtrationThe solid is collected by filtration
  2. dissolutiondissolved in methylene chloride
  3. customThe solution is dried
  4. concentrationconcentrated on a steam bath
  5. additionSkellysolve B is added to the boiling solution
  6. temperatureCooling

Sources & evidence

ORD record
ord-03e71bfeed07495489e538e57225e0ab
Source dataset
uspto-grants-1976_10
Patent number
US03987087

Reaction notes

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