Hydrochloric Acid → HCID 54140770, compound

HRID 1731167Notes

Reaction equation

HRID 1731167 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([CH3:23])(Br)[C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1.Cl>>[C:1]([C:9]1[CH:10]=[C:11]([CH2:15][CH:16]=[C:17]([CH3:23])[C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 21495651HCID 21495651, compound

Product 1

HCID 54140770HCID 54140770, compoundYield 53.7%

Conditions

Temperature
160 °C

Procedure

A mixture of 1.46 g of methyl 4-(m-benzoyl-phenyl)-2-methyl-2-bromo-butanoate and 7.3 ml of quinoline was heated at 160° C for 3 hours and after cooling to room temperature, 73 ml of 2N hydrochloric acid were added thereto. The mixture was extracted with methylene chloride and the organic phase was washed with 2N hydrochloric acid, with aqueous saturated sodium bicarbonate solution and then with water. The solution was dried over sodium sulfate, treated with activated carbon, filtered and evaporated to dryness under reduced pressure. The residue was chromatographed over magnesium silicate and eluted with methylene chloride to obtain 615 mg of methyl 4-(m-benzoylphenyl)-2-methyl-2-butenoate in the form of an oil.

Workup

  1. temperatureafter cooling to room temperature
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe organic phase was washed with 2N hydrochloric acid, with aqueous saturated sodium bicarbonate solution
  4. dry with materialThe solution was dried over sodium sulfate
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was chromatographed over magnesium silicate
  9. washeluted with methylene chloride

Sources & evidence

ORD record
ord-5a241b3614b64492bbf72d765d78e106
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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