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

HRID 2289883Notes

Reaction equation

HRID 2289883 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-3a629db9434b481fb3268a40cae4fede
Source dataset
uspto-grants-2000_07
Patent number
US06093856

Reaction notes

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