Triphenylphosphine → Phosphonium, (6-hydroxyhexyl)triphenyl-, bromide

HRID 366995Notes

Reaction equation

HRID 366995 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[Br-:1].[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 779706-Bromo-1-hexanol

Product 1

HCID 2784664Phosphonium, (6-hydroxyhexyl)triphenyl-, bromideYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 5 L, 3 neck round bottom flask fitted with nitrogen inlet, condenser, thermometer, mechanical stirring and nitrogen outlet is added 6-bromo-1-hexanol (500 g, 2.76 mol), triphenylphosphine (768 g, 2.9 mol) and acetonitrile (1800 ml) under nitrogen. The reaction mixture is heated to reflux for 72 hrs. The reaction mixture is cooled to room temperature and transferred into a 5 L beaker. The product is recrystallized from anhydrous ethyl ether (1.5 L) at 10° C. Vacuum filtration of the mixture followed by washing the white crystals with ethyl ether and drying in a vacuum oven at 50° C. for 2 hrs. gives 1140 g of the desired product.

Workup

  1. customInto a 5 L, 3 neck round bottom flask fitted with nitrogen inlet, condenser
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 72 hrs
  4. customThe product is recrystallized from anhydrous ethyl ether (1.5 L) at 10° C
  5. filtrationVacuum filtration of the mixture
  6. washby washing the white crystals with ethyl ether
  7. customdrying in a vacuum oven at 50° C. for 2 hrs

Sources & evidence

ORD record
ord-b8e9983d7c6546aea31c97e12e366129
Source dataset
uspto-grants-2000_10
Patent number
US06133222

Reaction notes

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