Hydrochloric Acid → Cyclohexanecarboxylic acid, 2,2-dimethyl-6-methylene-, methyl ester

HRID 2050786Notes

Reaction equation

HRID 2050786 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[C:10]([O:12][CH3:13])=[O:11].C([Li])CCC.C[Si](Cl)(C)C.Cl>O1CCCC1.CCCCCC>[CH3:8][C:4]1([CH3:9])[CH2:5][CH2:6][CH2:7][C:2](=[CH2:1])[CH:3]1[C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 58511249815-58-9HCID 178418339Butyllithium

Product 1

HCID 11095260Cyclohexanecarboxylic acid, 2,2-dimethyl-6-methylene-, methyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of methyl 2,6,6-trimethyl-cyclohex-1-ene-carboxylate (80.0 g) in tetrahydrofuran (THF, 640 ml), contained in a 1.5 l flask equipped with a mechanical strirrer and a nitrogen inlet, was deprotonated by adding, between -10° and 0°, a solution of butyllithium in hexane (411 ml of a 1.5M solution). Once the addition was completed, the reaction was allowed to proceed at 15°-17° for 10 min. The temperature was reduced to -30° and trimethylsilyl chloride (143.35 g) was added to the reaction mixture over half an hour, while maintaining the temperature at 10° or below. The temperature was allowed to increase to 20° and the reaction mixture was poured on 5% HCl. After stirring for 10 min, the mixture was extracted with ether and the organic phase was washed with saturated aqueous solutions of NaHCO3 and NaCl, dried over Na2SO4, filtered and the solvents evaporated. After distillation on a column filled with inox helices and equipped with a total reflux top, two fractions of a crude product were obtained.

Workup

  1. customequipped with a mechanical strirrer and a nitrogen inlet
  2. additionby adding, between -10° and 0°
  3. additionOnce the addition
  4. customwas reduced to -30°
  5. temperaturewhile maintaining the temperature at 10° or below
  6. temperatureto increase to 20°
  7. extractionthe mixture was extracted with ether
  8. washthe organic phase was washed with saturated aqueous solutions of NaHCO3 and NaCl
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customthe solvents evaporated
  12. distillationAfter distillation on a column
  13. additionfilled with inox helices
  14. customequipped with a total reflux top, two fractions of a crude product
  15. customwere obtained

Sources & evidence

ORD record
ord-61cf04297d2f46abb041bf213a4178a6
Source dataset
uspto-grants-1991_05
Patent number
US05015625

Reaction notes

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