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

HRID 1279199Notes

Reaction equation

HRID 1279199 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-a89d2627d3b4442f97a1dbd6c96ca025
Source dataset
uspto-grants-2002_09
Patent number
US06448213B1

Reaction notes

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