Sodium Bicarbonate → 2-(3-Hydroxyphenyl)-2-methylpropanal

HRID 1650064Notes

Reaction equation

HRID 1650064 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[CH:16]=[O:17])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+].[H][H]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[CH:16]=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 198553592-(3-(Benzyloxy)phenyl)-2-methylpropanalHCID 178418361HCID 178418361, compound

Product 1

HCID 198553382-(3-Hydroxyphenyl)-2-methylpropanalYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 38.9 g. (0.153 mole) of 2-(3-benzyloxyphenyl)-2-methylpropanal, 20 g. 5% Pd/C/50% water, 1.0 sodium bicarbonate and 150 ml. ethanol was shaken overnight under 55 psi of hydrogen. The reaction was filtered through diatomaceous earth, the filter cake washed with ethanol and the combined filtrate evaporated. The residue was reduced as above for another 8 hours. Another 10 g. portion of catalyst was added and the reaction continued overnight. The reaction was worked-up as above and the residue purified via column chromatography on 500 g. of silica gel eluted with 25% ether-hexane to yield 14 g. (56%) of the title compound as an oil.

Workup

  1. additionA mixture of 38.9 g
  2. filtrationThe reaction was filtered through diatomaceous earth
  3. washthe filter cake washed with ethanol
  4. customthe combined filtrate evaporated
  5. customwas reduced as above for another 8 hours
  6. additionportion of catalyst was added
  7. customthe reaction continued overnight
  8. custompurified via column chromatography on 500 g
  9. washof silica gel eluted with 25% ether-hexane
  10. customto yield 14 g

Sources & evidence

ORD record
ord-881042301aa04aefacc253a82acdb6e8
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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