HCID 59266385, compound → 1219689-98-1

HRID 1189711Notes

Reaction equation

HRID 1189711 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:14][CH3:15])[C:8]([CH2:12][OH:13])=[CH:9]2)=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].CC(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:14][CH3:15])[C:8]([CH:12]=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59266385HCID 59266385, compound

Product 1

HCID 592664311219689-98-1

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

In a 500 ml three-necked bottle, 34.1 g of 7-bromo-3-methoxy-2-naphthylcarbinol (0.128 mol) and 350 ml of acetone were added, and the mixture was stirred vigorously to form a solution. 167 g of active manganese dioxide (1.92 mol) was added to the solution, and the mixture was stirred at room temperature for 48 h to complete the reaction. The mixture was filtered, and the manganese dioxide filter cake was washed with ethyl acetate (200 ml*6). The filtrates were combined, and dried under vacuum in a rotary dryer to obtain a crude product as a yellow solid, which was recrystallized from methanol to obtain 29.3 g with a yield of the two steps of 86%.

Workup

  1. customto form a solution
  2. stirringthe mixture was stirred at room temperature for 48 h
  3. customthe reaction
  4. filtrationThe mixture was filtered
  5. filtrationthe manganese dioxide filter cake
  6. washwas washed with ethyl acetate (200 ml*6)
  7. customdried under vacuum in a rotary dryer

Sources & evidence

ORD record
ord-a507bb17ab1c4d1686c2cc057b310c31
Source dataset
uspto-grants-2014_03
Patent number
US08674136B2

Reaction notes

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