4-Hydroxy-3-(2-propen-1-yl)benzyl alcohol → 4-(Hydroxymethyl)-2-propylphenol

HRID 257835Notes

Reaction equation

HRID 257835 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:10][CH:11]=[CH2:12].[H][H]>C(O)C.[Rh]>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 539952564-Hydroxy-3-(2-propen-1-yl)benzyl alcoholHCID 178418361HCID 178418361, compound

Product 1

HCID 220112094-(Hydroxymethyl)-2-propylphenol

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.370 g (2.25 mmol) of the product of Step E dissolved in 25 mL of absolute ethanol was added 53 mg of a 5% rhodium on carbon catalyst and the mixture was shaken under a 40 psig pressure of hydrogen on a Parr apparatus. After 30 minutes, the reaction mixture was removed, filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 35% ethyl acetate/hexane to afford the title compound.

Workup

  1. customthe reaction mixture was removed
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residue was purified on a silica gel flash chromatography column
  5. washeluted with 35% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7d6f4515d9f24da1b52d7ab461658b23
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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