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

HRID 2115630Notes

Reaction equation

HRID 2115630 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 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-aee88950c23841b8a0c804c2330088b3
Source dataset
uspto-grants-2008_10
Patent number
US07435861B2

Reaction notes

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