Sodium borohydride → 4-Chloro-2,6-dimethylbenzyl alcohol

HRID 842008Notes

Reaction equation

HRID 842008 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([CH2:6][OH:7])=[C:8]([CH3:10])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18406975HCID 18406975, compound

Product 1

HCID 695457014-Chloro-2,6-dimethylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-chloro-2,6-dimethyl benzaldehyde (5.0 g, 168.64 g/mol) in 100 mL dry methanol. Cool to 0° C. while stirring under N2. Portionwise add powdered NaBH4 (0.76g, 37.85 g/mol) over 5 minutes. Stir at 0° C. for 2 hours, monitoring by TLC until aldehyde consumed, then evaporate to a yellow oil. Add H2O (50 mL) and bring to pH. 7.0 by addition of saturated NH4Cl. Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) and dry the pooled organic layers over Na2SO4. Filter and concentrate to a yellow oil. Flush through a pad of silica to remove baseline material, then evaporate to a yellow solid (3.0 g) which can be used without further purification. LCMS=171.6 (MH+), 169.6 (M−)

Workup

  1. stirringStir at 0° C. for 2 hours
  2. custommonitoring by TLC until aldehyde consumed
  3. customevaporate to a yellow oil
  4. addition7.0 by addition of saturated NH4Cl
  5. extractionExtract the neutral aqueous layer with CH2Cl2 (3×75 mL)
  6. dry with materialdry the pooled organic layers over Na2SO4
  7. filtrationFilter
  8. concentrationconcentrate to a yellow oil
  9. customFlush through a pad of silica
  10. customto remove baseline material
  11. customevaporate to a yellow solid (3.0 g) which
  12. customcan be used without further purification

Sources & evidence

ORD record
ord-8a9ea758d80142898e4d4bb121c89fc1
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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