beta-Phenylisovaleric acid → 3,3-Dimethyl-1-indanone
Reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4]([OH:6])=O>S(=O)(=O)(O)O>[CH3:7][C:2]1([CH3:1])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:6])[CH2:3]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
3-Methyl-3-phenyl-butanoic acid (247.2 g, 1.39 mol) was placed in a flask and warmed to 130° C. Sulphuric acid 95% (180 ml) was then added over 4 min and the mixture was stirred at 130° C. for 1 h, after which more sulphuric acid (10 ml) was added. After stirring for 45 min, the dark solution was poured onto ice (500 g) and extracted with hexane (200 ml). The organic phase was washed with NaHCO3 (50 ml), dried (MgSO4) and evaporated. The remaining oil was distilled in vacuo (78°0,065 Torr) to give 3,3-dimethyl-1-indanone (157.5 g).
Workup
- stirringAfter stirring for 45 min
- additionthe dark solution was poured onto ice (500 g)
- extractionextracted with hexane (200 ml)
- washThe organic phase was washed with NaHCO3 (50 ml)
- dry with materialdried (MgSO4)
- customevaporated
- distillationThe remaining oil was distilled in vacuo (78°0,065 Torr)
Sources & evidence
- ORD record
- ord-a443cbaa6a454a2d9b5bc434d8bb29d1
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538243B2
Reaction notes
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