Sodium borohydride → 2,6-Dimethyl4-isopropylbenzyl alcohol

HRID 1595449Notes

Reaction equation

HRID 1595449 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH3:15])[C:5]=1[CH:6]=[O:7]>C(O)C.Cl.O>[CH3:15][C:8]1[CH:9]=[C:10]([CH:12]([CH3:13])[CH3:14])[CH:11]=[C:4]([CH3:3])[C:5]=1[CH2:6][OH:7]

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 154807002,6-Dimethyl-4-isopropylbenzaldehyde

Product 1

HCID 154807012,6-Dimethyl4-isopropylbenzyl alcoholYield 87%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium borohydride (0.04 g, 1.04 mmol) in 90% ethanol (5 mL) was added dropwise to a solution of 2,6-dimethyl-4-isopropylbenzaldehyde (Example 1) (0.55 g, 3.1 mmol) in absolute ethanol (5 mL). The reaction mixture was allowed to stir at room temperature for 1 hour, then heated at 60° C. for 30 min. The solution was cooled to 0° C. and the unreacted sodium borohydride was decomposed by the addition of a few drops of 3N HCl. The solvent was removed under reduced pressure to give a red oil which was suspended in water (10 mL) and extracted with ether (2×20 mL). The ether was removed under reduced pressure to afford a red oil which was purified by flash chromatography using silica gel (eluted with hexane-EtOAc, 93:3) to give 0.48 g (87%) of the title compound as a white solid; mp 75-77° C.

Workup

  1. temperatureheated at 60° C. for 30 min
  2. temperatureThe solution was cooled to 0° C.
  3. customThe solvent was removed under reduced pressure
  4. customto give a red oil which
  5. extractionextracted with ether (2×20 mL)
  6. customThe ether was removed under reduced pressure
  7. customto afford a red oil which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-97972046f3b742209044f11a923dac78
Source dataset
uspto-grants-2001_09
Patent number
US06288101B1

Reaction notes

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