p-[(E)-2-(4,4-dimethyl-6-chromanyl)propenyl]benzyl alcohol → p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzaldehyde

HRID 2118523Notes

Reaction equation

HRID 2118523 reaction equation
[CH3:1][C:2]1([CH3:23])[C:7]2[CH:8]=[C:9](/[C:12](/[CH3:22])=[CH:13]/[C:14]3[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1([CH3:23])[C:7]2[CH:8]=[C:9](/[C:12](/[CH3:22])=[CH:13]/[C:14]3[CH:15]=[CH:16][C:17]([CH:18]=[O:19])=[CH:20][CH:21]=3)[CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 13478154p-[(E)-2-(4,4-dimethyl-6-chromanyl)propenyl]benzyl alcohol

Product 1

HCID 13478159p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzaldehydeYield 70.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

0.5 g of p-[(E)-2-(3,4-dihydro-4,4-dimethyl-1-benzopyran-6-yl)propenyl]benzyl alcohol was dissolved in 20 ml of methylene chloride and the solution is treated with 10 g of manganese dioxide. After stirring at room temperature for 6 hours, the solid material is filtered off, rinsed well with methylene chloride and the filtrate was evaporated. After recrystallization of the residue from hexane/ether, there are obtained 350 mg of p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzaldehyde of melting point 102°-104° C.

Workup

  1. filtrationthe solid material is filtered off
  2. washrinsed well with methylene chloride
  3. customthe filtrate was evaporated
  4. customAfter recrystallization of the residue from hexane/ether, there

Sources & evidence

ORD record
ord-e2da091dd2814b96a6b33c1b2a832e00
Source dataset
uspto-grants-1987_07
Patent number
US04678793

Reaction notes

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