1-Bromooctadecane → Stearyltriphenylphosphonium Bromide

HRID 435567Notes

Reaction equation

HRID 435567 reaction equation
[CH2:1]([Br:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[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>C1(C)C=CC=CC=1>[Br-:19].[C:33]1([P+:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 82181-BromooctadecaneHCID 11776Triphenylphosphine

Product 1

HCID 11786690Stearyltriphenylphosphonium Bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenyl-n-octadecylphosphonium bromide is prepared by refluxing n-octadecyl bromide (1000 grams) and triphenyl phosphine (787 grams) in about 1400 ml. of toluene for 16 hours at about 110° C. The product is precipitated from the cooled solution by the addition of about 500 ml. of ethyl acetate and the crystals filtered from solution. These crystals, 1550 grams, are added to 890 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 3000 ml. of water which is heated to 80°-85° C. and stirred for 1 hour. The oil layer is washed twice with about 2000 ml. of room-temperature water, then dried at 50° C. under nitrogen for 16 hours at a pressure less than 100 torr. The product, triphenyl-n-octadecylphosphonium 3,5-dicarbomethoxybenzenesulfonate, solidifies on cooling.

Workup

  1. customThe product is precipitated from the cooled solution by the addition of about 500 ml
  2. filtrationof ethyl acetate and the crystals filtered from solution
  3. additionThese crystals, 1550 grams, are added to 890 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 3000 ml
  4. temperatureof water which is heated to 80°-85° C.
  5. washThe oil layer is washed twice with about 2000 ml
  6. dry with materialof room-temperature water, then dried at 50° C. under nitrogen for 16 hours at a pressure less than 100 torr
  7. temperatureon cooling

Sources & evidence

ORD record
ord-32bb2b18d2d84ea69b81d517bc8899c7
Source dataset
uspto-grants-1977_02
Patent number
US04006123

Reaction notes

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