Diethylene Glycol Monoethyl Ether → 4-(2-Fluorophenyl)butanoic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9]CC#N.[OH-:13].[Na+].C(OCCO[CH2:21][CH2:22][OH:23])C>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:21][C:22]([OH:23])=[O:13]Participants
4
Procedure
15.4 gm of the compound prepared in (5) above was added to a mixture of 400 ml of 5% aqueous solution of sodium hydroxide and 400 ml of diethylene glycol monoethyl ether. The mixture was heated under reflux for 3.5-hours, cooled to room temperature, and washed with ether. After the addition of concentrated hydrochloric acid to acidify, the water layer was extracted twice with 500 ml of ethyl acetate. The extract was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 15.9 gm of the title compound.
Workup
- temperatureThe mixture was heated
- temperatureunder reflux for 3.5-hours
- washwashed with ether
- additionAfter the addition of concentrated hydrochloric acid
- extractionthe water layer was extracted twice with 500 ml of ethyl acetate
- washThe extract was washed with water and saturated brine in this order
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-f4ab671fd27e4cd0864eecd8bb4e9c11
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05834476
Reaction notes
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