Lithium hydroxide, monohydrate → HCID 59333716, compound
Reaction equation
[F:1][CH2:2][CH:3]([O:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])[CH2:4][F:5].O.[OH-].[Li+]>C1COCC1.O>[F:1][CH2:2][CH:3]([O:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:4][F:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Benzyl 2-(1,3-difluoropropan-2-yloxy)acetate (0.91 g, 3.73 mmol) was dissolved in THF (14 mL)/water (7 mL) mixture and treated with lithium hydroxide monohydrate (0.469 g, 11.18 mmol) and allowed to stir for 16 hours at room temperature. The mixture was concentrated, redissolved in water and extracted with ethyl acetate. The aqueous phase was treated with 2M HCl and NaCl then extracted with ethyl acetate (3×). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title product (0.388 g, 67% yield).
Workup
- concentrationThe mixture was concentrated
- dissolutionredissolved in water
- extractionextracted with ethyl acetate
- additionThe aqueous phase was treated with 2M HCl and NaCl
- extractionthen extracted with ethyl acetate (3×)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-324763c68e9b4012a214af574076c7ed
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188101B2
Reaction notes
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