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2-Methyl-2-butene → 2-Difluoromethyloxy-4,6-dimethylphenyl acetic acid

HRID 352352
Notes
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Reaction equation

HRID 352352 reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[CH2:12][CH:13]=[O:14].CC(=CC)C.P([O-])(O)(O)=[O:22].[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[CH2:12][C:13]([OH:22])=[O:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 186846932-Difluoromethyloxy-4,6-dimethylphenylacetaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 227093292-Difluoromethyloxy-4,6-dimethylphenyl acetic acidYield 14%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6386tert-ButanolSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

19.2 g of 2-difluoromethyloxy-4,6-dimethylphenylacetaldehyde (XXXIV-c-1) as the crude product were dissolved in 270 ml of tert-butanol, the solution was mixed with 90.4 g of 2-methyl-2-butene, and a solution of 90 g of sodium dihydrogen phosphate and 42 g of sodium chlorite in 353 ml of water was subsequently added dropwise at room temperature. The mixture was stirred for four hours and then stirred into 400 ml of ethyl acetate, and the phases were separated. The aqueous phase was extracted two more times using ethyl acetate, and the combined organic phases were dried over magnesium sulphate and concentrated. After stirring with hexane, 11 g of solid were isolated, from which 2.5 g (14% of theory via 2 steps) of 2-difluoromethyloxy-4,6-dimethylphenylacetic acid of melting point 124-127° C. were obtained.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted two more times
  3. dry with materialthe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated
  5. stirringAfter stirring with hexane

Sources & evidence

ORD record
ord-791c1f8aa2a6468f94d242303c753131
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06746990B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes