Potassium Hydroxide → HCID 22610224, compound

HRID 2290505Notes

Reaction equation

HRID 2290505 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[C:7]2[CH2:6][C:5](C(OCC)=O)([C:13]([O:15]CC)=[O:14])[CH2:4][C:3]1=2.[OH-].[K+]>C(O)C.O>[CH3:11][C:8]1([CH3:12])[CH2:9][CH2:10][C:2]([CH3:1])([CH3:23])[C:3]2[CH2:4][CH:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]1=2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20230955HCID 20230955, compound

Product 1

HCID 22610224HCID 22610224, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

18.4 g of diethyl 4,5,6,7-tetrahydro-4,4,7,7-tetramethyl-2,2-indanebiscarboxylate are dissolved in 500 ml of ethanol and treated with a solution of 64 g of potassium hydroxide in a mixture of 200 ml of ethanol and 50 ml of water. After heating at reflux temperature for 6 hours, the mixture is cooled, the majority of the alcohol is distilled off on a rotary evaporator, the residue is poured on to ice, acidified with 2N hydrochloric acid, extracted repeatedly with ethyl acetate, dried and evaporated. The thus-obtained crude product is heated to 160° C. for 5.5 hours and subsequently chromatographed on silica gel [eluting agent: hexane/ether (2:1)]. After recrystallization from pentane, there are obtained 6.5 g of 4,5,6,7-tetrahydro-4,4,7,7-tetramethyl-2-indanecarboxylic acid in the form of colourless crystals of melting point 125°-129° C.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 6 hours
  3. temperaturethe mixture is cooled
  4. distillationthe majority of the alcohol is distilled off on a rotary evaporator
  5. additionthe residue is poured on to ice
  6. extractionextracted repeatedly with ethyl acetate
  7. customdried
  8. customevaporated
  9. customThe thus-obtained crude product
  10. customsubsequently chromatographed on silica gel [eluting agent: hexane/ether (2:1)]
  11. customAfter recrystallization from pentane, there

Sources & evidence

ORD record
ord-98129af05a7b460f88addb7cb02c0187
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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