Hydroquinone → 2-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

HRID 894154Notes

Reaction equation

HRID 894154 reaction equation
O1C=CC=[CH:2]1.[C:6]1([CH:13]=[CH:12][C:10](O)=[CH:9][CH:8]=1)[OH:7].P([O-])([O-])([O-])=O.P([O-])(O)(O)=O.[K+].P([O-])([O-])(O)=O.[Na+].[Na+].[Cl-].[Na+].[O:34]1[CH2:39][CH2:38]OCC1.O>O>[CH3:2][C:38]1[CH:39]([OH:34])[CH2:13][C:6](=[O:7])[C:8]=1[CH2:9][CH:10]=[CH2:12]

Participants

9

Reactant 7

HCID 785HydroquinoneHCID 1061PhosphateHCID 5234Sodium ChlorideHCID 8029FuranHCID 24203Sodium Phosphate, DibasicHCID 516951Monobasic potassium phosphateHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-Yield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Three hundred milligrams of a furan compound of the formula (II) (R1 =CH3, R2 =--CH2 --CH=CH2, R3 =CH3) was added to a dioxane/water mixture (dioxane 3.0 ml, water 2.0 ml), and then hydroquinone (10 mg) was added thereto. To the solution was added a phosphate buffer solution [a solution of potassium dihydrogen phosphate (0.27 g) and sodium monohydrogen phosphate (0.36 g) in water (5.0 ml)], followed by refluxing for 90 minutes. After adding water (10 ml) to the reaction solution, the solution was saturated with sodium chloride and extracted twice with ether. The ether layer was dried over magnesium sulfate, and the solvent was removed by evaporation. By column chromatography on silica gel, 135 mg of allethrolone (2-methyl-3-allyl-cyclopent-2-en-4-on-1-ol) was obtained.

Workup

  1. temperatureby refluxing for 90 minutes
  2. extractionextracted twice with ether
  3. dry with materialThe ether layer was dried over magnesium sulfate
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-c87a9378d5354bfba944264cf07e67ab
Source dataset
uspto-grants-1981_08
Patent number
US04282372

Reaction notes

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