Ethylene Glycol → HCID 15965627, compound

HRID 2080927Notes

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-1330e4ea90b44c2d87c83c034ed5ede9
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932416B2

Reaction notes

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