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

HRID 2050786노트

반응식

HRID 2050786 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 5851121-Cyclohexene-1-carboxylic acid, 2,6,6-trimethyl-, methyl esterHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-61cf04297d2f46abb041bf213a4178a6
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05015625

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