Ozone → 3-phenylbutane-1,3-diol

HRID 450963Notes

Reaction equation

HRID 450963 reaction equation
[C:1]1([C:7]([OH:12])([CH2:9][CH:10]=C)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:13]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[C:1]1([C:7]([OH:12])([CH3:8])[CH2:9][CH2:10][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24823OzoneHCID 1437612-Phenyl-4-penten-2-olHCID 4311764Sodium borohydride

Product 1

HCID 113240913-phenylbutane-1,3-diol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-phenylpent-4-en-2-ol (74 g, 0.457 mol) in dry CH2Cl2 (1 L) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4 (42.8 g, 1.143 mol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-phenylbutane-1,3-diol (67.8 g), which was used for the next step without purification.

Workup

  1. customThe system was then flushed with oxygen
  2. customto remove excess ozone
  3. customThe mixture was quenched with water
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-39e87bb1bc9548cca74618f4df874bcb
Source dataset
uspto-grants-2013_07
Patent number
US08487094B2

Reaction notes

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