Diethyl Ether → HCID 23459452, compound

HRID 2287124Notes

Reaction equation

HRID 2287124 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[C:12]1([C:18]2([CH:24]([CH3:29])[C:25](OC)=[O:26])[CH:23]=[CH:22][CH2:21][CH:20]=[CH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>O>[CH3:29][CH:24]([C:18]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:23]=[CH:22][CH2:21][CH:20]=[CH:19]1)[CH2:25][OH:26]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 23459442HCID 23459442, compound

Product 1

HCID 23459452HCID 23459452, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.76 g. of lithium aluminum hydride is placed in 20 ml. of absolute ether. 2.42 g. of methyl 2-(1-phenyl-2,5-cyclohexadien-1-yl)-propionate in 20 ml. of absolute ether are added dropwise thereto. After stirring at room temperature for 5 hours, the mixture is worked-up as follows: The mixture is treated with ethyl acetate and water, filtered under suction and the organic phase is separated from the aqueous phase. The organic phase is dried with sodium sulfate, filtered and evaporated. The crude product obtained is chromatographed on 80 g. of silica gel with ether/petroleum ether (1:2), oily β-methyl-1-phenyl-2,5-cyclohexadien-1ethanol being obtained.

Workup

  1. filtrationfiltered under suction
  2. customthe organic phase is separated from the aqueous phase
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product obtained
  7. customis chromatographed on 80 g

Sources & evidence

ORD record
ord-41133877685d4951b4516c54055cf65e
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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