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

HRID 1858902Notes

Reaction equation

HRID 1858902 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 followed by washing with ethyl ether and drying in a vacuum oven at 50° C for 2 hrs. gives 1140 g of the desired product as white crystals.

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
  6. washby washing with ethyl ether
  7. customdrying in a vacuum oven at 50° C for 2 hrs

Sources & evidence

ORD record
ord-47956b9465824e85b771138e64b35000
Source dataset
uspto-grants-2000_11
Patent number
US06153577

Reaction notes

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