Lithium Hydroxide → (2Z)-3-Methylhepta-2,6-dienoic acid
Reaction equation
[CH3:1]/[C:2](/[CH2:8][CH2:9][CH:10]=[CH2:11])=[CH:3]/[C:4]([O:6]C)=[O:5].[Li+].[OH-]>C1COCC1.O>[CH3:1]/[C:2](/[CH2:8][CH2:9][CH:10]=[CH2:11])=[CH:3]/[C:4]([OH:6])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of the title compound from Example 20 (6.8 g, 32.5 mmol) in THF (150 mL) was treated with 1 N LiOH (100 mL) and water (125 mL) and stirred vigorously for 4 days. The mixture was diluted with water and washed twice with ether. The aqueous phase was taken to pH 1.5 by addition of 2N HCl and extracted three times with ether. The organic extracts were dried and the solvents evaporated to give the title compound (2.57 g, 56%) as a pale yellow oil.
Workup
- washwashed twice with ether
- additionThe aqueous phase was taken to pH 1.5 by addition of 2N HCl
- extractionextracted three times with ether
- customThe organic extracts were dried
- customthe solvents evaporated
Sources & evidence
- ORD record
- ord-95275c8a89bf41fbbcba0190e95a8163
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07666861B2
Reaction notes
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