HCID 72460980, compound → 2,6,11,15-Tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedial

HRID 1296855Notes

Reaction equation

HRID 1296855 reaction equation
[CH3:1][C:2](=[CH:5][CH:6]=[CH:7][C:8]([CH3:22])=[CH:9][CH:10]=[CH:11][CH:12]=[C:13]([CH3:21])[CH:14]=[CH:15][CH:16]=[C:17]([CH3:20])[CH2:18][OH:19])[CH2:3][OH:4]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:20][C:17](=[CH:16][CH:15]=[CH:14][C:13]([CH3:21])=[CH:12][CH:11]=[CH:10][CH:9]=[C:8]([CH3:22])[CH:7]=[CH:6][CH:5]=[C:2]([CH3:1])[CH:3]=[O:4])[CH:18]=[O:19]

Participants

4

Reactant 1

HCID 72460980HCID 72460980, compound

Product 1

HCID 252018972,6,11,15-Tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedialYield 73.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2,6,11,15-tetramethyl-hexadeca-2,4,6,8,10,12,14-heptaene-1,16-diol (50 g, 0.166 mol) in 3000 mL of DCM was added portionwise manganese dioxide (500 g, 5.75 mol) at room temperature. The mixture 15 was After heated to reflux for 2 h, the solid was filtered via celite and washed with CH2Cl2. The solvent was removed under reduced pressure to give 36 g of pure product (73%). 1H-NMR (300 Hz DMSO-d6) δ 9.42 (s, 2H, CHO), 7.18 (s, 1H, CH), 7.16 (s, 1H, CH), 6.93 (m, 6H, CH), 2.01 (s, 6H, CH3), 1.82 (s, 6H, CH3).

Workup

  1. temperatureAfter heated
  2. temperatureto reflux for 2 h
  3. filtrationthe solid was filtered via celite
  4. washwashed with CH2Cl2
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dbb5c5766c5b4bcaa61acd0467e04a70
Source dataset
uspto-grants-2007_07
Patent number
US07247752B2

Reaction notes

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