Octane → Triphenyl{[4-(propan-2-yl)phenyl]methyl}phosphanium chloride

HRID 1979856Notes

Reaction equation

HRID 1979856 reaction equation
CCCCCCCC.[CH:9]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][Cl:17])=[CH:14][CH:13]=1)([CH3:11])[CH3:10].[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[Cl-:17].[CH:9]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][P+:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 356OctaneHCID 11776TriphenylphosphineHCID 749164-Isopropylbenzyl chloride

Product 1

HCID 23321400Triphenyl{[4-(propan-2-yl)phenyl]methyl}phosphanium chlorideYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A large round-bottom flask was obtained and into this flask was charged 150 ml (102.4 g) n-octane having 99% purity, 84.6 g para-isopropylbenzyl chloride and 111.5 g triphenylphosphine. The reaction solution was heated to 95°-100° C. and maintained at that temperature for approximately 29 hours. At that time the heat was turned off and the reaction solution was cooled and charged with 197.5 methyl alcohol to dissolve the suspended solids. The methanol solution was then washed twice with 50 ml of octane each time. The octane was decanted off, leaving 383.7 g of a methyl alcohol solution of 45% para-isopropylbenzyl triphenylphosphonium chloride in methanol.

Workup

  1. customA large round-bottom flask was obtained and into this flask
  2. temperatureThe reaction solution was heated to 95°-100° C.
  3. temperaturemaintained at that temperature for approximately 29 hours
  4. temperaturethe reaction solution was cooled
  5. dissolutionto dissolve the suspended solids
  6. washThe methanol solution was then washed twice with 50 ml of octane each time
  7. customThe octane was decanted off

Sources & evidence

ORD record
ord-78d99f1dba7c4914ad3534a76bdec0be
Source dataset
uspto-grants-1984_11
Patent number
US04482751

Reaction notes

Loading…