Hydrogen Peroxide → 5-p-t-Butylphenoxy-1-pentanol
Reaction equation
[C:1]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C2CCCCCCCC2)BCCCCCCC1.[OH-:35].[Na+].OO>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:35])=[CH:15][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]Participants
6
Procedure
The 5-(p-tert-butylphenoxy)-1-pentene (10.5 g) was treated with 115 ml 0.5 M 9-borabicyclononane in tetrahydrofuran and the reaction mixture was stirred at reflux for one hour. The solution was cooled to room temperature and treated with 25 ml 3 N sodium hydroxide, then 10 ml 30% hydrogen peroxide. After the bubbling ceased the reaction mixture was partitioned between 150 ml ether -150 ml water. The ether layer ws removed, dried (MgSO4), and evaporated to a yellow oil which was chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent) yielding a yellow oil which was vacuum distilled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g.
Workup
- temperatureat reflux for one hour
- customwas partitioned between 150 ml ether -150 ml water
- customThe ether layer ws removed
- dry with materialdried (MgSO4)
- customevaporated to a yellow oil which
- customwas chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent)
- customyielding a yellow oil which
- distillationdistilled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g
Sources & evidence
- ORD record
- ord-88bb89b2e47545ba958f918de5d8f738
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04543362
Reaction notes
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