Hydrogen Peroxide → 3-(4-Bromophenyl)propan-1-ol

HRID 1715386Notes

Reaction equation

HRID 1715386 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[OH-].[Na+].OO.CC[O:17]CC>C1COCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH2:3][OH:17])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 137529Benzene, 1-bromo-4-(2-propenyl)-

Product 1

HCID 105606143-(4-Bromophenyl)propan-1-olYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

BH3 (1M in THF, 412 mL, 412 mmol) is added to a sol. of 1-allyl-4-bromo-benzene (204 g, 1.03 mmol) in THF (1.00 L) under nitrogen at 0° C. The mixture is stirred overnight while warming up to rt. Aq. NaOH (2.5M, 1.65 L, 4.12 mol) is added, and the mixture is cooled to 0° C. H2O2 (35%, 480 mL, 5.15 mol) is dropped carefully, and the mixture is stirred for 3 h. Et2O is added, and the phases are separated. The org. layer is washed with water (1×), and brine (1×). The org. layer is dried over MgSO4, filtered, and the solvents are removed under reduced pressure. Purification by FC (Et2O/petroleum ether 1:1→Et2O) yields the title compound (97.4 g, 44%).

Workup

  1. temperaturethe mixture is cooled to 0° C
  2. stirringthe mixture is stirred for 3 h
  3. customthe phases are separated
  4. washlayer is washed with water (1×), and brine (1×)
  5. dry with materiallayer is dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents are removed under reduced pressure
  8. customPurification by FC (Et2O/petroleum ether 1:1→Et2O)

Sources & evidence

ORD record
ord-7353017194dd4a8eb89a2568fd8e7473
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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