Hydrochloric Acid → HCID 54140770, compound

HRID 1579766Notes

Reaction equation

HRID 1579766 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(Cl)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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 21495651HCID 21495651, compound

Product 1

HCID 54140770HCID 54140770, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

Sources & evidence

ORD record
ord-5516a56319dc46b6a2c0a132ccee17b1
Source dataset
uspto-grants-1976_01
Patent number
US03931302

Reaction notes

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