Acetic Acid → HCID 67082468, compound

HRID 1943547Notes

Reaction equation

HRID 1943547 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH: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][CH: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][C:6]1[CH:11]=[CH: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][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 23665763Sodium BisulfiteHCID 67082438HCID 67082438, compound

Product 1

HCID 67082468HCID 67082468, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound (19) (10.0 g) and acetic acid (50 ml) were put in a reaction vessel under a nitrogen atmosphere, hydrogen peroxide (31% aqueous solution; 4.5 ml) was added dropwise thereto in the temperature range of 25° C. to 30° C., and the mixture was stirred for another 2 hours at room temperature. Then, the reaction mixture was poured into a vessel containing an aqueous solution sodium hydrogensulfite (100 ml) and ethyl acetate (200 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of 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. The solvent was distilled off under reduced pressure, giving 8.9 g of 4′-butoxy-4-hydroxy-2,3-difluoro-1,1′-biphenyl (20). The yield based on the compound (19) was 97.9%.

Workup

  1. additionThen, the reaction mixture was poured into a vessel
  2. additionmixed
  3. customhad separated into two phases of 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. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cb2f94e478494d2ba8fd99e6fbe28a19
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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