Ethyl Bromide → HCID 15818605, compound

HRID 1576600Notes

Reaction equation

HRID 1576600 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 ethyl-magnesium bromide, prepared from 3.64 g. (0.15 mole) of magnesium and 16.4 g. of ethyl bromide in ether. After stirring for one 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]cycloheptane 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]cycloheptane 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-c03521e15c87447b82d1739f8d7afe0a
Source dataset
uspto-grants-1976_09
Patent number
US03981917

Reaction notes

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