Ethanol → 4,5,10,11-tetrahydro-1H-dibenzo[a,d]cycloheptene-5-ethanol

HRID 2308847Notes

Reaction equation

HRID 2308847 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][CH2:17][OH:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)C.[Cl-].[NH4+]>O1CCCC1>[CH2:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([CH2:16][CH2:17][OH:18])[C:7]=2[CH2:15][CH:14]=[CH:13]1

Participants

5

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 1852151710,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol

Product 1

HCID 201879344,5,10,11-tetrahydro-1H-dibenzo[a,d]cycloheptene-5-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 80.0 g of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol, 195.7 ml of dry ethanol, 2.0 l of dry tetrahydrofuran and 3.2 l of dry distilled ammonia, stirred under argon, is treated at -30° to -31° with 25.09 g of sodium (3 to 4 pieces). After the exothermic reaction has faded, the mixture is stirred for about an additional 10 minutes and subsequently treated portionwise with a total of 60 g of ammonium chloride. After removal of the ammonia, the suspension remaining is washed three times with 800 ml of saturated ammonium chloride solution each time. The aqueous extracts are extracted twice with 1.5 l of ether each time. The organic phases are washed with 800 ml of water, combined, dried and evaporated in vacuo. There is obtained crude 4,5,10,11-tetrahydro-1H-dibenzo[a,d]cycloheptene-5-ethanol in the form of an oil which is used in the next step without further purification.

Workup

  1. customof dry
  2. distillationdistilled ammonia
  3. additionis treated at -30° to -31° with 25.09 g of sodium (3 to 4 pieces)
  4. customAfter the exothermic reaction
  5. stirringthe mixture is stirred for about an additional 10 minutes
  6. customAfter removal of the ammonia
  7. washthe suspension remaining is washed three times with 800 ml of saturated ammonium chloride solution each time
  8. extractionThe aqueous extracts are extracted twice with 1.5 l of ether each time
  9. washThe organic phases are washed with 800 ml of water
  10. customdried
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-185c53779acc410d905a0fa3274eb6c5
Source dataset
uspto-grants-1987_09
Patent number
US04691040

Reaction notes

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