Hydrochloric Acid → 3-(2,6-Dimethylphenyl)benzyl alcohol

HRID 2422258Notes

Reaction equation

HRID 2422258 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=1.[BH4-].[Na+].Cl>COCCOC.O1CCCC1>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 230828662',6'-Dimethylbiphenyl-3-carbaldehyde

Product 1

HCID 230827203-(2,6-Dimethylphenyl)benzyl alcoholYield 83.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2′,6′-Dimethylbiphenyl-3-carbaldehyde (18.5 g, 88.0 mmol) was dissolved in a mixture of 1,2-dimethoxyethane (100 mL) and tetrahydrofuran (100 mL), and sodium borohydride (1.66 g, 44.0 mmol) was added under ice-cooling and the mixture was stirred at the same temperature for 3 hrs and then at room temperature for 3 hrs. Dil. hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-50% ethyl acetate/hexane) to give the title compound (15.6 g, yield 83%) as a colorless oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. waitat room temperature for 3 hrs
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (10%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f104b5d1f6e84016b5d9239ed896992d
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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