HCID 10937342, compound → HCID 11068396, compound

HRID 274539Notes

Reaction equation

HRID 274539 reaction equation
[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([CH:13]([OH:23])[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[O:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13](=[O:23])[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[O:26][CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10937342HCID 10937342, compound

Product 1

HCID 11068396HCID 11068396, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 9.0 g of 4-(benzyloxy)-3-methoxy-α-(3-phenylpropyl)benzyl alcohol in 250 ml of methylene chloride is treated with 90 g of manganese dioxide and held at the reflux temperature for 2 hours. After cooling, the precipitate is filtered under suction and washed with methylene chloride. The filtrate is evaporated and the residue is recrystallized from ethyl acetate/ether. There is obtained 4'-(benzyloxy)-3'-methoxy-4-phenylbutyrophenone in the form of colorless crystals of m.p. 81°-82°.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered under suction
  3. washwashed with methylene chloride
  4. customThe filtrate is evaporated
  5. customthe residue is recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-eeae8644a3d44d1f96b00b1c8f618902
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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