1,6-Dibromohexane → HCID 13536971, compound

HRID 981136Notes

Reaction equation

HRID 981136 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][OH:11].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[S:2][CH3:1]

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 20071482HCID 20071482, compound

Product 1

HCID 13536971HCID 13536971, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

2-(Methylthio)benzeneethanol (2.0 g) and 1,6-dibromohexane (9.31 g) were stirred rapidly at room temperature with tetrabutylammonium bisulphate (0.34 g) and 12.5 M aqueous sodium hydroxide (11 ml) for 16 h. The mixture was diluted with water (45 ml), extracted with ER (3×55 ml) and the combined organic extracts were washed consecutively with water (45 ml) and brine (45 ml), dried and evaporated. The residual oil (8.84 g) was purified by [FCS] using ER-cyclohexane (0:100→2:98) as eluent to give the title compound. T.l.c. (Cyclohexane--ER, 79:1) Rf 0.17.

Workup

  1. extractionextracted with ER (3×55 ml)
  2. washthe combined organic extracts were washed consecutively with water (45 ml) and brine (45 ml)
  3. customdried
  4. customevaporated
  5. customThe residual oil (8.84 g) was purified by [FCS]

Sources & evidence

ORD record
ord-56903d5df6f54002bc630bd21d7332e3
Source dataset
uspto-grants-1991_02
Patent number
US04990505

Reaction notes

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