Chloroform → Ethyl 3,3-dimethyl-7-chloroheptanoate

HRID 1659005Notes

Reaction equation

HRID 1659005 reaction equation
[CH3:1][C:2]([CH3:12])([CH2:7][CH2:8][CH2:9][CH2:10][Cl:11])[CH2:3][C:4](O)=[O:5].[CH:13](Cl)(Cl)Cl.S(Cl)(Cl)=O.CN(C)[CH:23]=[O:24]>>[CH3:1][C:2]([CH3:12])([CH2:7][CH2:8][CH2:9][CH2:10][Cl:11])[CH2:3][C:4]([O:24][CH2:23][CH3:13])=[O:5]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 20465694HCID 20465694, compound

Product 1

HCID 21767804Ethyl 3,3-dimethyl-7-chloroheptanoate

Procedure

To a solution of 3,3-dimethyl-7-chloroheptanoic acid (428 g., 2.21 moles) in 3 l. of chloroform containing 3 ml. of N,N-dimethylformamide is added 500 ml. of thionyl chloride and the resulting solution is tested under reflux for 3 hours. The reaction solution then is concentrated in vacuo and the residual acid chloride is dissolved in a minimum amount of benzene and added slowly to a solution containing 1260 ml. of 95% ethanol and 2520 ml. of benzene and 390 ml. of collidine. After heating under reflux for 1 hour, the solution is concentrated and the residue is dissolved in ether washed with water, dilute sodium bicarbonate solution and saline solution, dried over magnesium sulfate and concentrated to give 415 g. of crude oil, which is distilled under vacuum to yield two fractions: 46.6 g. boiling at 75°C. (0.3 mm.) and 236.7 g. boiling at 75° - 80°C. (0.3 mm). The total yield is 283.3 g. (60%) and the product is indicated to be 95% pure by g.l.c.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationThe reaction solution then is concentrated in vacuo
  3. dissolutionthe residual acid chloride is dissolved in a minimum amount of benzene
  4. additionadded slowly to a solution
  5. additioncontaining 1260 ml
  6. temperatureAfter heating
  7. temperatureunder reflux for 1 hour
  8. concentrationthe solution is concentrated
  9. dissolutionthe residue is dissolved in ether
  10. washwashed with water, dilute sodium bicarbonate solution and saline solution
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated
  13. customto give 415 g
  14. distillationof crude oil, which is distilled under vacuum
  15. customto yield two fractions

Sources & evidence

ORD record
ord-ae7f146d8e244567ad6c7c8d7ff4f069
Source dataset
uspto-grants-1976_06
Patent number
US03966773

Reaction notes

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