Hydrochloric Acid → HCID 54124948, compound
Reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].O.Cl>CCCCCC>[CH:6]([C:8]1([C:6]([O:5][CH2:4][CH3:3])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14])=[CH:8][CH2:9][CH3:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Sodium hydride, 60% in mineral oil (8.3 g, 200 mmol) was washed with 2 portions of hexane and then dried under an N2 flow. This was suspended in dimethylformamide and ethyl 2-cyclohexanonecarboxylate (34.1 g, 200 mmol) was added slowly under N2 (note the foaming and exotherm), with cooling with a 25° C. water bath. After complete addition, the mixture was stirred at 25° C. for ~1 hour and the treagents added. The stirring mixture was heated to 50° C. for 18 hours (overnight). The reaction was then cooled to room temperature. The entire mixture was poured into water, neutralized with dilute HCl and extracted with two portions of 1:1 ether-hexane The combined organics were then washed with two portions of water followed by saturated brine, then dried over MgSO4, filtered and stripped giving 41.8 g of an impure mixture of products. Purification of the product by chromatography (silica gel,: 5% methyl t-butyl ether/90% hexane) gave 28.4 g of the title compound.
Workup
- customdried under an N2 flow
- additionAfter complete addition
- additionthe treagents added
- temperatureThe stirring mixture was heated to 50° C. for 18 hours (overnight)
- temperatureThe reaction was then cooled to room temperature
- extractionextracted with two portions of 1:1 ether-hexane The combined
- washorganics were then washed with two portions of water
- dry with materialdried over MgSO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-2b950e854fb14a7b96744a37d51f1dae
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046211
Reaction notes
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