Hydrochloric Acid → 3-(Oxan-2-yl)propanoic acid
Reaction equation
[OH-].[Li+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([O:13]C)=[O:12].Cl>O1CCCC1>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([OH:13])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
An aqueous solution of lithium hydroxide (4 mL of 2 M) was added to a solution of methyl 3-(tetrahydro-2H-pyran-2-yl)propionate (Preparation 5, 0.46 g, 2.67 mmol) in tetrahydrofuran (16 mL) and the reaction mixture was heated under reflux for 10 h. The cooled reaction mixture was acidified with aqueous 2N hydrochloric acid to pH 1, and then extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (30 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a colourless oil (460 mg, 67%).
Workup
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 10 h
- customThe cooled reaction mixture
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined extracts were washed with brine (30 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-db4df99109974cbbbaadd1768aaa6b15
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07012083B2
Reaction notes
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