Hydrochloric Acid → 5-Cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 1637669Notes

Reaction equation

HRID 1637669 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+].Cl>C1COCC1>[CH:1]1([C:11]2([OH:21])[C:12]3[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=3[CH2:14][CH2:15][C:16]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]2=3)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14589DibenzosuberoneHCID 25517Ammonium ChlorideHCID 178418630HCID 178418630, compound

Product 1

HCID 192613825-Cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cyclopropylmagnesium bromide in dry THF (prepared from cyclopropylbromide (12.1 g, 0.10 mol), magnesium turnings (2.45 g, 0.10 mol) and dry THF (65 ml)) was placed under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (10.4 g, 0.05 mol) in dry THF (25 ml) was added dropwise and when addition was complete the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled on an ice-bath and saturated ammonium chloride (50 ml) was carefully added. The mixture was neutralized with 2N hydrochloric acid and extracted with diethyl ether (2×200 ml). The combined organic extracts were dried (Na2SO4) and the solvent was evaporated in vacuo to give 13.1 g of crude 5-cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol.

Workup

  1. additionwhen addition
  2. temperaturewas heated
  3. temperatureat reflux for 30 minutes
  4. temperatureThe reaction mixture was cooled on an ice-bath
  5. extractionextracted with diethyl ether (2×200 ml)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fccfa773af944852aebb2f5e2fe55a3f
Source dataset
uspto-grants-2000_03
Patent number
US06043239

Reaction notes

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