Water → HCID 22421025, compound

HRID 129280

Reaction equation

HRID 129280 reaction equation
C(NC(C)C)(C)C.[CH:8]1([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1.[C:22](Cl)(=[O:24])[CH3:23].O>O1CCCC1.CCCCCC>[C:22]([C:11]1([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9][CH:8]([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12]1)(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 7198Dimethyl 1,4-cyclohexanedicarboxylateHCID 7912Diisopropylamine

Product 1

HCID 22421025HCID 22421025, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Di-isopropylamine (44.7 ml) was dissolved in dry tetrahydrofuran (400 ml) and cooled to -78° C. under nitrogen with mechanical stirring. A solution of B-butyllithium in hexane (1.6M, 197 ml) was added. After stirring at -78° C. for 10 minutes a solution of dimethyl cyclohexane-1,4-dicarboxylate (56.6 g, Lancaster) in tetrahydrofuran (200 ml) was added. After stirring for a further 30 minutes at -78° C. a solution of acetyl chloride (22.5 ml) in tetrahydrofuran (200 ml) was added. The reaction mixture was allowed to warm up to room temperature over a period of 3 hours. Water was then added and the mixture extracted with ether. The ethereal extracts were washed with water, saturated sodium bicarbonate solution, dilute hydrochloric acid and brine, and then were dried over anhydrous magnesium sulphate. Evaporation under reduced pressure gave a colourless oil which was slowly distilled to yield dimethyl 1-acetylcyclohexane-1,4-dicarboxylate (23.3 g, b.pt. 114°-120 C. at 0.4 mmHg).

Workup

  1. additionwas added
  2. additionwas added
  3. temperatureto warm up to room temperature over a period of 3 hours
  4. extractionthe mixture extracted with ether
  5. washThe ethereal extracts were washed with water, saturated sodium bicarbonate solution, dilute hydrochloric acid and brine
  6. dry with materialwere dried over anhydrous magnesium sulphate
  7. customEvaporation under reduced pressure
  8. customgave a colourless oil which
  9. distillationwas slowly distilled

Sources & evidence

ORD record
ord-7a01cc761f6a426c93cc4b606233d47c
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Linked notes

Loading…