Diethylene Glycol Monoethyl Ether → 2-Fluoro-4-methylbenzoic acid
Reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6]C=1C#N.[OH-:11].[K+].C(OCCO[CH2:19][CH2:20][OH:21])C>>[F:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:19]=1[C:20]([OH:21])=[O:11]Participants
4
Procedure
Compound of Step 1 (14 g, 105 mmol, 1 eq) was dissolved in 2-(2-ethoxyethoxy) ethanol (105 mL) and KOH (105 ml of a 8 M solution, 840 mmol, 8 eq) was added, the mixture was refluxed under nitrogen for 3 hours. The mixture was cooled and the pH set to 3. The product was extracted with EtOAc and the organic layer was washed 3 times with water and dried with sodium sulfate. The crude mixture was purified on silica using a 0-3% acetic acid/toluene gradient. 3.1 g of the desired compound (19%) was obtained.
Workup
- temperaturethe mixture was refluxed under nitrogen for 3 hours
- temperatureThe mixture was cooled
- extractionThe product was extracted with EtOAc
- washthe organic layer was washed 3 times with water
- dry with materialdried with sodium sulfate
- customThe crude mixture was purified on silica using a 0-3% acetic acid/toluene gradient
Sources & evidence
- ORD record
- ord-a91ec33f9e2d448db6eb3a4af5341245
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06583126B2
Reaction notes
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