Hydrochloric Acid → (R)-4-methylcyclohex-3-enecarboxylic acid
Reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][C@H]2C(C)(C)COC2=O)=[O:9])[CH2:4][CH:3]=1.O.[OH-].[Li+].Cl>C1COCC1.O.CO>[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH:3]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
(R)—((S)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl) 4-methylcyclohex-3-enecarboxylate 502 (1.30 g, 5.15 mmol) in THF (10 mL), water (1 mL) and methanol (1 mL) was treated with lithium hydroxide monohydrate (2.16 g, 51.5 mmol) and warmed to 50° C. with stirring. After 1 hour, the reaction mixture treated with 1M HCl. The mixture was extracted with hexanes:THF (10:1), dried over sodium sulfate, filtered and concentrated to 0.738 g (quantitative yield) of (R)-4-methylcyclohex-3-enecarboxylic acid 503 as a white powder.
Workup
- extractionThe mixture was extracted with hexanes:THF (10:1)
- dry with materialdried over sodium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-aec370a1b79246398725be01d5f6b84a
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09393256B2
Reaction notes
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