Acetone → HCID 21717622, compound

HRID 1386484Notes

Reaction equation

HRID 1386484 reaction equation
C[C:2]1[C:3]([CH:16]([C:19]2[CH:26]=[CH:25]C(C#N)=[CH:21][CH:20]=2)[CH:17]=[CH2:18])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[OH-:27].[K+].C[C:30]([CH3:32])=[O:31]>CCCCCC>[CH3:13][C:9]1([CH3:12])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]2[CH:4]=[C:3]([CH:16]([C:19]3[CH:20]=[CH:21][C:32]([C:30]([OH:27])=[O:31])=[CH:25][CH:26]=3)[CH:17]=[CH2:18])[CH:2]=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 21717629HCID 21717629, compound2×

Product 1

HCID 21717622HCID 21717622, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A suspension of the derivative (E) 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzonitrile (0.44 g, 1.20 mmol) in solution in alcoholic potassium hydroxide (0.94 g, 16.8 mmol KOH in 0.55 ml H2O and 3.3 ml EtOH) is heated to reflux under magnetic stirring for 4 hours. The progress of the reaction is followed by CCM (eluent acetone:hexane=10:90). The ethanol is evaporated in a rotary evaporator, the product taken up in water (50 ml), acidified with 1N HCl and extracted 3 times with ether. The ether phase is dried with MgSO4, filtered and evaporated to obtain, after washing with pentane and drying, 0.40 g of a white powder the acid (E) 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzoic acid (yield=96%).

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. customThe ethanol is evaporated in a rotary evaporator
  4. extractionextracted 3 times with ether
  5. dry with materialThe ether phase is dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain
  9. washafter washing with pentane
  10. customdrying

Sources & evidence

ORD record
ord-abb588c78e4948a4ae9099422558f4d8
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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