Hydrochloric Acid → Ethyl cyclohexanoate

HRID 1655507Notes

Reaction equation

HRID 1655507 reaction equation
C([OH:3])C.C(N([CH2:9][CH3:10])CC)C.[CH:11]1([C:17](Cl)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl>C1(C)C=CC=CC=1.O>[CH:11]1([C:17]([O:18][CH2:9][CH3:10])=[O:3])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 18686Ethyl cyclohexanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of ethanol (45 ml) and triethylamine (78 g) in toluene (120 ml), cyclohexane carbonyl chloride (75 g, 0.51 mol) was added dropwise at 15° C. or lower, and stirring was continued for 3 h at room temperature. The reaction mixture was poured into cold H2O (350 ml), acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic extract was washed thrice with H2O (150 ml), dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The residue (93 g) was distilled under reduced pressure to give the title compound as a colorless oil; yield: 64 g; bp 101°-102° C./35 mmHg (Lit: bp 194° C./~760 torr: G. A. Olah, T. Keumi, D. Meider, Synthesis, 1978, 929.).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed thrice with H2O (150 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. customthe solvent was removed in vacuo
  6. distillationThe residue (93 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-ba2aa70f3f864d30920289569e182201
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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