Water → Cyclohexa-1,3-dienecarboxylic acid butyl ester

HRID 1437314Notes

Reaction equation

HRID 1437314 reaction equation
[CH2:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH:9]1OC(=O)C)=[O:7])[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].O>O1CCCC1>[CH2:1]([O:5][C:6]([C:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 587439042-Acetoxycyclohex-3-enecarboxylic acid butyl ester

Product 1

HCID 58743894Cyclohexa-1,3-dienecarboxylic acid butyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Crude butyl ester (a) (55.25 g, max 0.207 mol) was dissolved in dry tetrahydrofuran (320 ml) and cooled in an ice/salt bath. To this was added slowly, over 1 hour, potassium t-butoxide in tetrahydrofuran (1 M, 220 ml, 0.22 mol). After 0.5 hour water and petroleum ether were added and the mixture filtered quickly through kieselguhr. The phases were separated and the aqueous extracted with more petroleum ether (×2). The combined organic extracts were washed with brine, dried and evaporated to give a mobile orange oil (31.85 g, 86%), which was used immediately without further purification.

Workup

  1. temperaturecooled in an ice/salt bath
  2. additionTo this was added slowly, over 1 hour
  3. filtrationthe mixture filtered quickly through kieselguhr
  4. customThe phases were separated
  5. extractionthe aqueous extracted with more petroleum ether (×2)
  6. washThe combined organic extracts were washed with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-0a525f1f8c9e442d969a093fdc5b63d5
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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