Sodium Chloride → Ethyl 7-(cyclohexan-1-on-2-yl)heptanoate

HRID 1439655Notes

Reaction equation

HRID 1439655 reaction equation
[C:1]1(=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].O.[C:18]1(C)C=CC(S(O)(=O)=O)=C[CH:19]=1.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>O.C1C=CC=CC=1.C(O)C>[C:1]1(=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:18][CH3:19])=[O:14]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 204657322-Oxocyclohexaneheptanoic acid

Product 1

HCID 12848421Ethyl 7-(cyclohexan-1-on-2-yl)heptanoate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 232 g. of 7-(cyclohexan-1-on-2yl)heptanoic acid in 2500 ml. of ethanol is refluxed for 4.5 hours with 3.8 g. of p-toluenesulfonic acid monohydrate. The solution is diluted with 200 ml. of benzene, and boiling is continued for 2 hours as 200 ml. of distillate is removed. The volume of the solution is concentrated to 500 ml. After dilution with 500 ml. of ether the solution is extracted with a solution prepared from 50 ml. of saturated sodium bicarbonate, 50 ml. of saturated sodium chloride, and 100 ml. of water. The extract is washed with saturated sodium chloride, dried, and evaporated. The product is purified by distillation to give a liquid, IR 1740 cm-1 (ester carbonyl) and 1715 cm-1 (ketone carbonyl).

Workup

  1. additionThe solution is diluted with 200 ml
  2. customof distillate is removed
  3. concentrationThe volume of the solution is concentrated to 500 ml
  4. extractionof ether the solution is extracted with a solution
  5. customprepared from 50 ml
  6. washThe extract is washed with saturated sodium chloride
  7. customdried
  8. customevaporated
  9. distillationThe product is purified by distillation
  10. customto give a liquid, IR 1740 cm-1 (ester carbonyl) and 1715 cm-1 (ketone carbonyl)

Sources & evidence

ORD record
ord-4a82193963b447c19fe19e7f7e7eb348
Source dataset
uspto-grants-1977_11
Patent number
US04060540

Reaction notes

Loading…