Sulfuric Acid → HCID 22789037, compound

HRID 1605646Notes

Reaction equation

HRID 1605646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11](/[C:14](/[CH3:18])=[CH:15]\C#N)=[CH:10][CH:9]=1.[Mg].CI.S(=O)(=O)(O)O.CC[O:29][CH2:30][CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11](/[C:14](/[CH3:18])=[CH:15]/[C:30](=[O:29])[CH3:31])=[CH:12][CH:13]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 21547164HCID 21547164, compound

Product 1

HCID 22789037HCID 22789037, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 23.7 gm (0.1 mol) of 3-(2'-fluoro-4-biphenylyl)-crotononitrile in 500 ml of dry methylene chloride was added dropwise over a period of 75 minutes to a Grignard reagent prepared from 12.2 gm (0.5 mol) of magnesium and 71 gm (0.5 mol) of methyl iodide in 500 ml of anhydrous ether, and the resulting mixture was refluxed for 4.5 hours. Thereafter, the cooled reaction mixture was stirred into a mixture consisting of 2 kg of ice and 100 ml of concentrated sulfuric acid. The organic phase was separated, washed with aqueous 1% sulfuric acid, then with water, then with a saturated aqueous sodium bicarbonate solution and again with water, dried over sodium sulfate, and evaporated in vacuo. The solid residue was recrystallized from cyclohexane, yielding 7.2 gm (28% of theory) of fallow crystalline (E)-4-(2'-fluoro-4-biphenylyl)-3-penten-2-one, m.p. 92°C.

Workup

  1. temperaturethe resulting mixture was refluxed for 4.5 hours
  2. customThereafter, the cooled reaction mixture
  3. customThe organic phase was separated
  4. washwashed with aqueous 1% sulfuric acid
  5. dry with materialwith water, then with a saturated aqueous sodium bicarbonate solution and again with water, dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe solid residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-09c388c1e49d4b499fbcce42f4fba37d
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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