Ethylene Glycol → HCID 15965627, compound

HRID 2250844Notes

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>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

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 (150 ml) and water (250 ml), and the mixture was filtered with suction. The phases of the filtrate were separated, and the aqueous phase was acidified with concentrated aqueous HCl solution, and the precipitated solid was filtered off with suction. 41.1 g (93%) of 2-methyl-4-pentafluorosulfuranylbenzoic 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-cdfc7add121f4811bc424537bb17c813
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317124B2

Reaction notes

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