HCID 22091595, compound → HCID 86753060, compound

HRID 2392939Notes

Reaction equation

HRID 2392939 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:18])=[CH:15]/[CH2:16][OH:17])[CH:5]=[CH:4][C:3]1=2>C(Cl)Cl.O=[Mn]=O>[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:18])=[CH:15]/[CH:16]=[O:17])[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 1

HCID 22091595HCID 22091595, compound

Product 1

HCID 86753060HCID 86753060, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

3.42 g (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-en-1-ol were dissolved in 23 ml of CH2Cl2 and treated with 16.1 g of MnO2. The reaction mixture was vigorously stirred at ambient temperature over night and then filtered through Celite. Evaporation of the solvent followed by flash chromatography (silica gel, hexane/AcOEt=92:8) afforded 2.86 g of (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enal as pale yellow oil.

Workup

  1. filtrationfiltered through Celite
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fa1d6937761c4971953b3d2f97c66048
Source dataset
uspto-grants-1998_09
Patent number
US05801253

Reaction notes

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