Hydrochloric Acid → HCID 22664966, compound

HRID 392592Notes

Reaction equation

HRID 392592 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Br[C:12]([CH3:19])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].Cl>CCOCC.[Zn]>[CH3:18][C:12]([C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])([CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 22664966HCID 22664966, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

2-Chlorobenzoyl chloride (17.5 g, 0.1 mol) and ethyl 2-bromo-2,2-dimethylacetate (19.5 g, 0.1 mol) were diluted with ether (200 ml) and added dropwise into a 300 ml four-necked flask containing a zinc powder (13.0 g, 0.2 mol). After adding dropwise about 30 ml, the mixture was heated and the remaining solution was added dropwise over 2 h under reflux. After the completion of the dropwise addition, the mixture was refluxed for 4 h and allowed to cool, and 1N-hydrochloric acid (100 ml) was added dropwise. After partitioning, the aqueous layer was extracted with ether (100 ml), and the organic layer was combined. The mixture was dried over sodium sulfate and concentrated. The concentrated dry solid was purified by silica gel column chromatography (silica gel 1 kg, hexane:ethyl acetate=9:1) to give the title compound (13.8 g, 54%) as a colorless oil.

Workup

  1. additionAfter adding dropwise about 30 ml
  2. temperaturethe mixture was heated
  3. additionthe remaining solution was added dropwise over 2 h
  4. temperatureunder reflux
  5. additionAfter the completion of the dropwise addition
  6. temperaturethe mixture was refluxed for 4 h
  7. temperatureto cool
  8. customAfter partitioning
  9. extractionthe aqueous layer was extracted with ether (100 ml)
  10. dry with materialThe mixture was dried over sodium sulfate
  11. concentrationconcentrated
  12. customThe concentrated dry solid
  13. customwas purified by silica gel column chromatography (silica gel 1 kg, hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8b40289cf0d844de95a6d4733f6b48ed
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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