1,6-Dibromohexane → (3-((6-Bromohexyl)oxy)propyl)benzene
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
6
Procedure
3-Phenylpropanol (3.00 g) and 1,6-dibromohexane (16.10 g, 10.2 ml) were stirred rapidly at RT with tetra-n-butylammonium hydrogen sulphate (0.5 g) and 12.5M aqueous NaOH (16 ml) for 30 h. The mixture was diluted with H2O (80 ml), extracted with ER (3×100 ml), and the combined organic extracts were washed consecutively with H2O (80 ml) and BR (80 ml). The dried extracts were evaporated and the residual oil purified by [FCS], eluting with CX (one columnful), followed by EA-CX (1:20) to give the title compound (5.35 g) as a colourless oil.
Workup
- extractionextracted with ER (3×100 ml)
- washthe combined organic extracts were washed consecutively with H2O (80 ml) and BR (80 ml)
- customThe dried extracts were evaporated
- customthe residual oil purified by [FCS]
- washeluting with CX (one columnful)
Sources & evidence
- ORD record
- ord-e60f1b243f79417d890fe9a5a2749425
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04992474
Reaction notes
Loading…