Methanol → HCID 11321052, compound

HRID 2293684Notes

Reaction equation

HRID 2293684 reaction equation
O[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C[OH:13]>[Pt]=O>[OH:13][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:3]([OH:4])[CH2:2][CH3:11]

Participants

4

Reactant 2

HCID 887MethanolHCID 1011212-Hydroxy-1-phenyl-1-propanone

Product 1

HCID 11321052HCID 11321052, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A mixture of platinum oxide (302 mg) in methanol (30 mL) is stirred under a hydrogen atmosphere (balloon) for 1 hr and then treated with 2-hydroxypropiophenone (2.00 g). The mixture is stirred under hydrogen for 4 hrs, the catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure to give an oily residue which is chromatographed on silica gel (230-400 mesh, 200 ), eluting with a gradient of ethyl acetate/hexane (5/95-20/80). Pooling of fractions with an Rf =0.41 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure gives the title compound.

Workup

  1. stirringThe mixture is stirred under hydrogen for 4 hrs
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customto give an oily residue which
  5. customis chromatographed on silica gel (230-400 mesh, 200 )
  6. washeluting with a gradient of ethyl acetate/hexane (5/95-20/80)
  7. customPooling of fractions with an Rf =0.41 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-9faee0e715d04031a6cfe9ca96a02af7
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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