Acetyl chloride → HCID 22421025, compound

HRID 1441035Notes

Reaction equation

HRID 1441035 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1([C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1.[C:27](Cl)(=[O:29])[CH3:28]>O1CCCC1.CCCCCC.O>[C:27]([C:16]1([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14][CH:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17]1)(=[O:29])[CH3:28]

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 7198Dimethyl 1,4-cyclohexanedicarboxylateHCID 7912DiisopropylamineHCID 178418339Butyllithium

Product 1

HCID 22421025HCID 22421025, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Di-isopropylamine (44.7 ml.) was dissolved in dry tetrahydrofuran (400 ml.) and cooled to -78° under nitrogen with mechanical stirring. A solution of n-butyllithium in hexane (1.6M, 197 ml.) was added. After stirring at -78° for 10 minutes a solution of dimethyl cyclohexane-1,4-dicarboxylate ((52.6 g.) Lancaster) in tetrahydrofuran (200 ml.) was added. After stirring for a further 30 minutes at -78° 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 were then 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.p. 114°-120°/0.4 mmHg). Nuclear Magnetic Resonance spectrum (NMR) was as follows: 3.89, 3H, s; 3.75, 3H, s; 2.6-1.4, 13H, m.

Workup

  1. temperaturecooled to -78° under nitrogen with mechanical stirring
  2. additionwas added
  3. additionwas added
  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 then 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-25150e6e8da549ef96f3bb702ca243a7
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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