Hydrochloric Acid → [3-(3-Methylphenoxy)phenyl]methanol

HRID 2422253Notes

Reaction equation

HRID 2422253 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[BH4-].[Na+].Cl>COCCOC.O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 230829033-(3-Methylphenoxy)benzaldehyde

Product 1

HCID 23083121[3-(3-Methylphenoxy)phenyl]methanolYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(3-Methylphenoxy)benzaldehyde (5.80 g, 27.3 mmol) was dissolved in a mixture of 1,2-dimethoxyethane (30 mL) and tetrahydrofuran (30 mL), sodium borohydride (0.567 g, 15.0 mmol) was added under ice-cooling and the mixture was stirred at the same temperature for 4 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 (20%-60% ethyl acetate/hexane) to give the title compound (4.83 g, yield 83%) as a pale-yellow oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a0d48e8ecff6423a8ad1266cb9971858
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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