Water → HCID 14851299, compound

HRID 1032446Notes

Reaction equation

HRID 1032446 reaction equation
O.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:12]=[C:11]([CH:20]([CH3:22])[CH3:21])[C:10]=2/[CH:23]=[CH:24]/[CH2:25][OH:26])=[CH:5][CH:4]=1>C1(C)C=CC=CC=1.[Mn]>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:12]=[C:11]([CH:20]([CH3:22])[CH3:21])[C:10]=2/[CH:23]=[CH:24]/[CH:25]=[O:26])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 962WaterHCID 14851298HCID 14851298, compound

Product 1

HCID 14851299HCID 14851299, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 1140TolueneSolvent

Procedure

Manganese IV dioxide (72.2 g, 0.83 mol) was suspended in toluene and refluxed for four hours with azeotropic removal of water. The unsaturated alcohol (28 g, 0.083 mol, Step B) was added and heating to reflux continued for 24 hours. The suspension was then cooled to room temperature and filtered through a bed of silica. The filtrate was concentrated in-vacuo to give 27.0 g of pure product (98%), mp 105°-107° C.

Workup

  1. temperatureheating
  2. temperatureto reflux
  3. filtrationfiltered through a bed of silica
  4. concentrationThe filtrate was concentrated in-vacuo

Sources & evidence

ORD record
ord-16b0334d02354e7f803557eb0df2a845
Source dataset
uspto-grants-1990_09
Patent number
US04957971

Reaction notes

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