Water → 4-(Hydroxymethyl)-3-methylbenzonitrile

HRID 1250280Notes

Reaction equation

HRID 1250280 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=C)[C:5]#[N:6].[O:12]=[O+][O-].[BH4-].[Na+].O>CO>[OH:12][CH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 183278913-Methyl-4-vinylbenzonitrile

Product 1

HCID 183278964-(Hydroxymethyl)-3-methylbenzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-70 °C

Procedure

3-Methyl-4-vinylbenzonitrile (0.40 g; 2.8 mmol; from step (i) above) was dissolved in 50 mL of methanol and cooled to −70° C. Ozone (2 eq.) was bubbled through, and then 0.20 g (5.3 mmol) of sodium borohydride and 5 mL of water were added and the cooling bath was removed. After 4 h the methanol was evaporated and the residue was partitioned between 1M HCl and ether. The aqueous layer was extracted twice with ether and the combined organic phase was washed with water, dried (Na2SO4) and evaporated to yield 0.37 g (90%) of the desired product, which was used in the next step without further purification.

Workup

  1. additionwere added
  2. customthe cooling bath was removed
  3. customAfter 4 h the methanol was evaporated
  4. customthe residue was partitioned between 1M HCl and ether
  5. extractionThe aqueous layer was extracted twice with ether
  6. washthe combined organic phase was washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-6aa23f0416354da883ddf147d9477e39
Source dataset
uspto-grants-2002_01
Patent number
US06337394B2

Reaction notes

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