Acetone → HCID 20538691, compound

HRID 1732487Notes

Reaction equation

HRID 1732487 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Cl.[Mg].[CH3:12][C:13]([CH3:15])=[O:14].Cl>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:13]([CH3:15])([OH:14])[CH3:12])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 76093,4-Dichlorobenzyl chlorideHCID 5462224Magnesium2×

Product 1

HCID 20538691HCID 20538691, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3,4-dichlorobenzylchloride (49.2 g, 0.254 mole) in dry ether (125 ml) was added dropwise during one hour to magnesium (6.08 g, 0.250 mole) in a three-necked flask equipped with stirrer and reflux condenser. Refluxing was continued until all the magnesium was dissolved and the solution was then cooled. Acetone (15.0 g, 0.258 mole) was added dropwise and the solution heated to reflux for three hours. After cooling the reaction mixture was poured out on ice (125 ml) and concentrated hydrochloric acid (23 ml). The phases were separated and the organic layer was washed with water, dried (Na2SO4) and evaporated in vacuum. The residual oil was distilled affording 1-(3,4-dichlorophenyl)-2-methyl-2-propanol (bp. 81°-83° C./0.2 mm Hg; 31.3 g, 57% yield). After several recrystallizations from petroleum ether the compound melted at 40°-41° C. The substituted propanol above (21.9 g, 0.100 mole) was mixed with dimethylaniline (12.4 g, 0.102 mole) and ether (50 ml). The solution was cooled and α-bromopropionyl bromide (21.4 g, 0.099 mole) was added dropwise during 40 minutes. Stirring at room temperature for 48 hours gave a crystalline precipitate of dimethylaniline hydrobromide, which was filtered off and washed with ether. The etheral solutions were combined and evaporated in vacuo. The residual oil was distilled affording 2-bromopropanoic acid 1-(3,4-dichlorophenyl)-2-methyl-2-propylester (bp. 135°-143° C./0.2 mm Hg; 19.2 g, 55% yield).

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. temperatureRefluxing
  4. dissolutionwas dissolved
  5. temperaturethe solution was then cooled
  6. temperaturethe solution heated
  7. temperatureto reflux for three hours
  8. temperatureAfter cooling the reaction mixture
  9. customThe phases were separated
  10. washthe organic layer was washed with water
  11. dry with materialdried (Na2SO4)
  12. customevaporated in vacuum
  13. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-12c54894e8bf4c5a8a23ad0c851ce25e
Source dataset
uspto-grants-1980_12
Patent number
US04237311

Reaction notes

Loading…