Hydrochloric Acid → HCID 69107744, compound

HRID 459698Notes

Reaction equation

HRID 459698 reaction equation
[CH3:1][C@@H:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C@H:3]1[C:10]([OH:12])=[O:11].[CH2:13](Br)[CH3:14].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[CH3:1][C@@H:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:8])([CH3:9])[C@H:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 18444190HCID 18444190, compound

Product 1

HCID 69107744HCID 69107744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

In a three necked 100 ml flask a suspension of trans-2,6,6-trimethyl-3-cyclohexene-1-carboxylic acid obtained in example 2 a) (0.800 g, 4.8 mmol), ethylbromide (0.616 g, 5.7 mmol) and K2CO3 (0.787 g, 5.7 mmol) in DMF (20 ml) was stirred at 40° C. for 2 h. The cooled reaction mixture was next poured onto cold 5% aqueous HCl and extracted twice with pentane. The organic phases were washed (three times with H2O and brine), dried (Na2SO4), filtered and concentrated. A bulb-to-bulb distillation (100°/4 mbar) afforded 0.870 g of ethyl trans 2,6,6-trimethyl-3-cyclohexene-1-carboxylate in the form of a trans/cis=96:4 mixture (yield=84%).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted twice with pentane
  3. washThe organic phases were washed (three times with H2O and brine)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationA bulb-to-bulb distillation (100°/4 mbar)

Sources & evidence

ORD record
ord-40518cd19b8f4d20ae0c3d624a936cf8
Source dataset
uspto-grants-2007_03
Patent number
US07196050B2

Reaction notes

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