Hydrogen Peroxide → 5-p-t-Butylphenoxy-1-pentanol

HRID 1493371Notes

Reaction equation

HRID 1493371 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

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 133137331-tert-Butyl-4-[(pent-4-en-1-yl)oxy]benzeneHCID 178418648HCID 178418648, compound

Product 1

HCID 133137345-p-t-Butylphenoxy-1-pentanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 5-(p-tert-butylphenoxy)-1-pentene (10.5 g) was treated with 115 ml 0.5M 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 3N 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 was 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

  1. temperatureat reflux for one hour
  2. customwas partitioned between 150 ml ether-150 ml water
  3. customThe ether layer was removed
  4. dry with materialdried (MgSO4)
  5. customevaporated to a yellow oil which
  6. customwas chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent)
  7. customyielding a yellow oil which
  8. 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-51fb0e7bbc244d4696a9614e3f2252da
Source dataset
uspto-grants-1991_06
Patent number
US05021460

Reaction notes

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