p-Toluenesulfonic acid → HCID 14997821, compound
Reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:17])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC>[OH:6][CH2:1][CH2:2][CH2:3][C:4]([O:17][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:5]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
To a mixture of 10 ml of gamma-butyrolactone and 40 ml of 1-decanol was added a crystal of p-toluenesulfonic acid. The reaction mixture was heated at 150° C. for 72 hours with stirring, cooled to room temperature, and then treated with 10 mg of sodium acetate. Flash chromatography (silica; 4:1 hexane:ethyl acetate eluent) afforded 5.6 g (17.7%) of 4-hydroxybutanoic acid, n-decyl ester as an oil.
Workup
- temperaturecooled to room temperature
Sources & evidence
- ORD record
- ord-fbc41837abc5464b898ae6b13b909055
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05036152
Reaction notes
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