1,6-Dibromohexane → HCID 23045317, compound

HRID 2108117Notes

Reaction equation

HRID 2108117 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+]>O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:12][CH2:11][CH2:10][CH2:9][S:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 131753393-[(4-Methylphenyl)sulfanyl]propan-1-ol

Product 1

HCID 23045317HCID 23045317, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[(4-Methylphenyl)thio]-1-propanol (4.0 g), 1,6-dibromohexane (16.06 g), 40% sodium hydroxide solution (40 ml) and TAB (1 g) were stirred together at room temperature for 18 h. The mixture was diluted with water (150 ml), extracted with ethyl acetate (2×150 ml), which was dried and evaporated in vacuo to give a colourless oil. Purification by FCC eluting with System A (0:20→1:19) gave the title compound (5.0 g) as a colourless oil. T.l.c. (System A 1:9) Rf 0.53.

Workup

  1. extractionextracted with ethyl acetate (2×150 ml), which
  2. customwas dried
  3. customevaporated in vacuo
  4. customto give a colourless oil
  5. customPurification by FCC
  6. washeluting with System A (0:20→1:19)

Sources & evidence

ORD record
ord-e112ca4b2b8d4e27afe84aa567dc4efa
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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