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

HRID 616468Notes

Reaction equation

HRID 616468 reaction equation
[CH2:1](O)[CH3:2].[OH2:4].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8](S(O)(=O)=O)=[CH:7][CH:6]=1.[C:16](=[O:19])(O)[O-:17].[Na+].[Cl-].[Na+].[CH:23]1C=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[C:6]1(=[O:4])[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[CH2:15][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:16]([O:17][CH2:1][CH3:2])=[O:19]

Participants

7

Reactant 5

HCID 241BenzeneHCID 702EthanolHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 232 g. of 7-(cyclohexan-1-on-2)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-2ca5932cdbfa45469327ed78ea15b36d
Source dataset
uspto-grants-1978_02
Patent number
US04074056

Reaction notes

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