Acetic Acid → HCID 67082440, compound

HRID 1943551Notes

Reaction equation

HRID 1943551 reaction equation
[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([F:21])[C:13]=2[F:22])=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH3:4].C(O)(=[O:25])C.OO.S([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:25])=[C:14]([F:21])[C:13]=2[F:22])=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 23665763Sodium BisulfiteHCID 59609876HCID 59609876, compound

Product 1

HCID 67082440HCID 67082440, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound (25) (8.5 g) and acetic acid (50 ml) were put in a reaction vessel under a nitrogen atmosphere, hydrogen peroxide (31% aqueous solution; 4.9 ml) was added dropwise thereto in the temperature range of 25° C. to 30° C., and the mixture was stirred for 2 hours at room temperature. Then, the reaction mixture was poured into a vessel containing an aqueous solution of sodium hydrogensulfite (100 ml) and ethyl acetate (200 ml), and mixed. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed sequentially with water and brine, and then dried over anhydrous magnesium sulfate. Then, the solvent is distilled off under reduced pressure, giving 2.8 g of 4-(4-butoxycyclohexenyl)-2,3-difluorophenol (26). The yield based on the compound (25) was 49.1%.

Workup

  1. additionThen, the reaction mixture was poured into a vessel
  2. additionmixed
  3. customhad separated into organic and
  4. extractionaqueous phases, and extraction into an organic phase
  5. customThe organic phase obtained
  6. washwashed sequentially with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, the solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-3e8f9c09210c456a9b466b15ec68a46a
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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