Acetonitrile → (5,6-Dihydroxyhexyl)triphenylphosphonium bromide

HRID 1578183Notes

Reaction equation

HRID 1578183 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:10][O:9]C(C)(C)[O:7]1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(#N)C>CC(C)=O>[Br-:1].[OH:7][CH:6]([CH2:10][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 46572524-(4-Bromobutyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 20555429(5,6-Dihydroxyhexyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 125 g. of 4-(4-bromobutyl)-2,2-dimethyl-1,3-dioxolane, 154 g. of triphenylphosphine, 800 ml. of acetonitrile, and 270 ml. of acetone is heated at reflux for 69 hours. The solvents are removed under vacuum, and the residue is treated with 250 ml. of chloroform and 15 ml. of water. The resulting mixture is stirred vigorously for 30 minutes. The solvents are removed with the aid of benzene chaser, and the solid product is washed with ether and dried under vacuum to give white crystals, m.p. 152°-170° C.

Workup

  1. temperatureat reflux for 69 hours
  2. customThe solvents are removed under vacuum
  3. additionthe residue is treated with 250 ml
  4. customThe solvents are removed with the aid of benzene chaser
  5. washthe solid product is washed with ether
  6. customdried under vacuum
  7. customto give white crystals, m.p. 152°-170° C.

Sources & evidence

ORD record
ord-987f5fbc9b7d42aba7f9bd29f5b61197
Source dataset
uspto-grants-1981_09
Patent number
US04291175

Reaction notes

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