Stearyl Alcohol → 1-Bromooctadecane

HRID 583954Notes

Reaction equation

HRID 583954 reaction equation
[CH2:1](O)[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].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:40]>C(Cl)Cl>[CH2:1]([Br:40])[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]

Participants

5

Reactant 3

HCID 8221Stearyl AlcoholHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 82181-BromooctadecaneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Octadecan-1-ol (1a) (520 mg, 1.92 mmol) and Ph3P (550 mg, 2.10 mmol) were dissolved in CH2Cl2 (25 mL). The mixture was cooled in an ice bath and CBr4 (630 mg, 1.90 mmol) was added with stirring. The mixture was allowed to warm to r.t. and was stirred overnight, then it was concentrated under a stream of N2 and the residue was subjected to flash column chromatography on silica, eluting with hexane, to afford 1-bromooctadecane (2a) (605 mg, 96%) as a waxy solid; mp 26-28° C.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringwas stirred overnight
  3. concentrationit was concentrated under a stream of N2
  4. washeluting with hexane

Sources & evidence

ORD record
ord-c2e7e0b3f60d4ab7a8e16d18e018b60c
Source dataset
uspto-grants-2005_08
Patent number
US06924309B2

Reaction notes

Loading…