Acetic Acid → 2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol

HRID 495171Notes

Reaction equation

HRID 495171 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH2:6][CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+].C(O)(=O)C>CO>[OH:12][CH2:7][CH2:6][CH:5]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:9]=1[OH:8])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 37916436-Methyl-4-phenyl-3,4-dihydrochromen-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 114819052-(3-Hydroxy-1-phenylpropyl)-4-methylphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-4-phenyl-chroman-2-one, 250 gins was stirred in 1.25 liters methanol at room temperature. Sodium borohydride 70 gms was added slowly, whilst maintaining the temperature at room temperature. The reaction mixture was stirred for 18 hours. After completion of reaction, the pH of the reaction mass was adjusted to pH 5 using acetic acid. The reaction mixture was concentrated under vacuum and 2 liters of water were added. The reaction mass was stirred for 30 minutes and the solids filtered. The solids were dried at 55° C. in a hot air oven for 20 hours. Weight 248 gms.

Workup

  1. customAfter completion of reaction
  2. concentrationThe reaction mixture was concentrated under vacuum and 2 liters of water
  3. additionwere added
  4. stirringThe reaction mass was stirred for 30 minutes
  5. filtrationthe solids filtered
  6. customThe solids were dried at 55° C. in a hot air oven for 20 hours

Sources & evidence

ORD record
ord-b89ea8bdaa984f07a70c766f2834209d
Source dataset
uspto-grants-2009_05
Patent number
US07538249B2

Reaction notes

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