1,6-Dibromohexane → HCID 23045298, compound

HRID 2108113Notes

Reaction equation

HRID 2108113 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 31236Phenoxyethanol

Product 1

HCID 23045298HCID 23045298, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Phenoxyethanol (2.76 g), 1,6-dibromohexane (14.6 g), TAB (1 g) and 50% sodium hydroxide (20 ml) were vigorously stirred for 21 h, added to water (100 ml) and extracted with diethyl ether (3×100 ml). The dried extract was evaporated and the residual colourless liquid (15 g) was purified by FCC eluting with cyclohexane followed by System A (1:1). Evaporation of the latter eluate gave the title compound (5.0 g) as a colourless liquid. T.l.c. (System A 1:1) Rf 0.6.

Workup

  1. extractionextracted with diethyl ether (3×100 ml)
  2. extractionThe dried extract
  3. customwas evaporated
  4. customthe residual colourless liquid (15 g) was purified by FCC
  5. washeluting with cyclohexane
  6. customEvaporation of the latter eluate

Sources & evidence

ORD record
ord-9f170953e6ac4cf99ea4e3acb8fbafb6
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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