Ethyl Bromide → HCID 15818605, compound

HRID 1284223Notes

Reaction equation

HRID 1284223 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:17]([Mg]Br)[CH3:18].[Mg].C(Br)C.[Cl-].[NH4+]>CCOCC>[CH2:17]([C:6]1([OH:16])[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH:9]=[CH:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)[CH3:18]

Participants

7

Reactant 5

HCID 6332Ethyl BromideHCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 178418443HCID 178418443, compound

Product 1

HCID 15818605HCID 15818605, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5H-dibenzo[a,d]cyclohepten-5-one (15.5 g., 0.075 mole) is added in portions to a solution of ethylmagnesium bromide, prepared from 3.64 g. (0.15 mole) of magnesium and 16.4 g. of ethyl bromide in ether. After stirring for 1 hour at room temperature, the mixture is heated to refluxing for 15 minutes, then cooled, and the Grignard adduct is hydrolyzed by cautiously adding ammonium chloride solution. The crude 5-ethyl-5-hydroxy-5H-dibenzo[a,d]cycloheptene is recovered from the ether layer in a yield of 16.78 g. (95%), m.p., 63°-65° (clearing at 70°C.). After recrystallization from petroleum ether, hexane and finally isopropyl alcohol, an analytical sample melted at 63°-65°C.

Workup

  1. customprepared from 3.64 g
  2. temperaturethe mixture is heated
  3. temperatureto refluxing for 15 minutes
  4. temperaturecooled
  5. customThe crude 5-ethyl-5-hydroxy-5H-dibenzo[a,d]cycloheptene is recovered from the ether layer in a yield of 16.78 g
  6. custom63°-65° (clearing at 70°C.)
  7. customAfter recrystallization from petroleum ether, hexane and finally isopropyl alcohol

Sources & evidence

ORD record
ord-a2cd9e04877f4a7f933b2414d1c73842
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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