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

HRID 900519Notes

Reaction equation

HRID 900519 reaction equation
[BH4-].[Na+].[OH-].[Na+].[CH3:5][C:6]1[CH:7]=[CH:8][C:9]2[O:14][C:13](=[O:15])[CH2:12][CH:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:22]=1.Cl>O.C(O)(C)C.C1CCCCC1.CC(C)=O>[OH:14][C:9]1[CH:8]=[CH:7][C:6]([CH3:5])=[CH:22][C:10]=1[CH:11]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:12][CH2:13][OH:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 37916436-Methyl-4-phenyl-3,4-dihydrochromen-2-oneHCID 4311764Sodium borohydride2×

Product 1

HCID 114819052-(3-Hydroxy-1-phenylpropyl)-4-methylphenolYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 21916603Acetone cyclohexaneSolvent

Procedure

A basic aqueous solution of sodium borohydride prepared beforehand by dissolving 23.8 g (0.630 moles) of NaBH4 at ambient temperature in 170 ml of H2O and 3.5 ml of 30% wt./vol. NaOH was added dropwise to a suspension of 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one of the formula (II) (100 g, 0.420 moles) in isopropanol (200 ml). Once addition was complete, the temperature was adjusted to 60° C. and the course of the reaction was monitored by TLC (eluent: cyclohexane/acetone: 70/30) until the substrate had completely disappeared. After 5 h, the reaction mixture was cooled to ambient temperature and HCl (2N) was added until a final pH of 7.0 was obtained. Stirring was continued for 30 min at ambient temperature, then the resultant suspension was filtered through a Buchner filter. The filtered solution was concentrated under reduced pressure and the crude residue was crystallised from toluene (280 ml) to yield 87.4 g (yield 86%) of 3-(2-hydroxy-5-methylphenyl)-3-phenylpropanol (VIII) as a white solid.

Workup

  1. additionOnce addition
  2. customwas adjusted to 60° C.
  3. customwas obtained
  4. waitwas continued for 30 min at ambient temperature
  5. filtrationthe resultant suspension was filtered through a Buchner
  6. filtrationfilter
  7. concentrationThe filtered solution was concentrated under reduced pressure
  8. customthe crude residue was crystallised from toluene (280 ml)

Sources & evidence

ORD record
ord-738e111c0df74c1dbf486ff147ca4876
Source dataset
uspto-grants-2008_04
Patent number
US07358399B2

Reaction notes

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