Diethyl Sulfate → 4,7-Methano-3aH-indene-3a-carboxylic acid, octahydro-, ethyl ester
Reaction equation
[OH-].[Na+].[CH:3]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH:8]1[C:4]2([C:13]([OH:15])=[O:14])[CH2:5][CH2:6][CH2:7]1.S(OCC)(O[CH2:20][CH3:21])(=O)=O>>[CH:3]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH:8]1[C:4]2([C:13]([O:15][CH2:20][CH3:21])=[O:14])[CH2:5][CH2:6][CH2:7]1Participants
Procedure
55.0 g (0.275 mole) of 20% aqueous sodium hydroxide solution was added dropwise to a mixture of 90.0 g (0.5 mole) of tricyclo[5.2.1.02,6 ]decane-2-carboxylic acid (mixture of endo and exo compounds) and 84.8 g (0.55 mole) of diethyl sulfate over one hour under stirring at 50 C.°. After completion of the addition, the stirring was continued at that temperature for 30 minutes. After completion of the stirring, the mixture was allowed to stand at room temperature for a while to form layers. The lower aqueous layer was taken out. The temperature was elevated again to 50 C.°. 55.0 g (0.275 mole) of a 20% aqueous sodium hydroxide solution was added dropwise to the remainder over one hour under stirring at that temperature for 30 minutes. Then, 16.5 g (0.0825 mole) of 20% aqueous sodium hydroxide solution was added thereto and the whole reaction mixture was stirred at 100 C.° for 45 minutes in order to decompose unreacted diethyl sulfate. The mixture was allowed to cool and divided into layers. After the distillation, 93.6 g (yield 90.0%) of pure ethyl tricyclo[5.2.1.02,6 ]decane-2-carboxylate was obtained.
Workup
- additionAfter completion of the addition
- customto stand at room temperature for a while
- customto form layers
- stirringunder stirring at that temperature for 30 minutes
- customthe whole reaction mixture
- stirringwas stirred at 100 C.° for 45 minutes in order
- temperatureto cool
- distillationAfter the distillation
Sources & evidence
- ORD record
- ord-d4fca5d240714f6cbd70f86f23da6b03
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04411828
Reaction notes
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