Hydrochloric Acid → HCID 107657770, compound

HRID 629432Notes

Reaction equation

HRID 629432 reaction equation
Cl([O-])=O.[Na+].[F:5][C:6]1[C:7]([OH:15])=[C:8]([CH:11]=[CH:12][C:13]=1[CH3:14])[CH:9]=[O:10].P([O-])(O)(O)=[O:17].[Na+].CC(=CC)C.Cl>C(O)(C)(C)C.O>[F:5][C:6]1[C:7]([OH:15])=[C:8]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:9]([OH:17])=[O:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 583831691283718-64-8

Product 1

HCID 107657770HCID 107657770, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To an aqueous solution (50.0 mL) of sodium chlorite (22.2 g) was added a mixture of 3-fluoro-2-hydroxy-4-methylbenzaldehyde (9.47 g), sodium dihydrogenphosphate (33.2 g) and 2-methyl-2-butene (32.5 mL) in tert-butanol (200 mL)-water (100 mL) under ice-cooling, and the mixture was stirred at the same temperature for 3 hr. The pH of the reaction mixture was adjusted to 2-3 with 2N hydrochloric acid. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (10.5 g) as a crude product. This compound was used in the next step without an additional purification.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a39058d3fa7d484c87a964c318345ef2
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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