Ethylene Glycol → HCID 15965627, compound
Reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([S:9]([F:14])([F:13])([F:12])([F:11])[F:10])=[CH:5][C:4]=1C)#N.[OH-:16].[Na+].[CH2:18]([OH:21])[CH2:19]O>CCOCC.O>[CH3:3][C:4]1[CH:5]=[C:6]([S:9]([F:14])([F:13])([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:19]=1[C:18]([OH:21])=[O:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 4-cyano-3-methylphenylsulfur pentafluoride (41.2 g, 169.4 g), NaOH (20.4 g, 510 mmol) and water (60 ml) in ethylene glycol (160 ml) was heated to 130° C. and stirred at this temperature for 4 h. It was then cooled to room temperature and diluted with MTB ether (150 ml) and water (250 ml), and the mixture was filtered with suction. The phases of the filtrate were separated, and the aqueous was acidified with concentrated aqueous HCl solution, and the precipitated solid was filtered off with suction. 41.1 g (93%) of 2-methyl-4-pentafluorosulfanylbenzoic acid were obtained as colorless crystals, m.p. 138-139° C.
Workup
- temperatureIt was then cooled to room temperature
- filtrationthe mixture was filtered with suction
- customThe phases of the filtrate were separated
- filtrationthe precipitated solid was filtered off with suction
Sources & evidence
- ORD record
- ord-90c08d91ff2a49b391423b0d04b81004
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07659429B2
Reaction notes
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