3-Methylcinnamic acid → 3-(3-Methylcyclohexyl)propanoic acid
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1>C(O)(=O)C>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:3]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
5% Ru/Al2O3 (3 g, 5 wt %), (2E)-3-(3-methylphenyl)acrylic acid (60 g, 0.37 mol) and acetic acid (300 mL) were charged into a 500 mL autoclave vessel. The mixture was vigorously stirred under a hydrogen atmosphere (40 bar) at 150° C., for 3 days. The catalyst was filtered and the product was dissolved in ethyl acetate (500 mL), washed with water (500 mL) and brine (500 mL). The organic phase was dried over sodium sulphate, filtered and evaporated to yield crude 3-(3-methylcyclohexyl)propanoic acid (60 g, 0.35 mol, 95% yield) as a colourless oil.
Workup
- filtrationThe catalyst was filtered
- dissolutionthe product was dissolved in ethyl acetate (500 mL)
- washwashed with water (500 mL) and brine (500 mL)
- dry with materialThe organic phase was dried over sodium sulphate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-395ffb6596814234a4e9633ecfd3b857
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08709994B2
Reaction notes
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