Hydrochloric Acid → 3-chloro-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cycloheptene

HRID 2071726Notes

Reaction equation

HRID 2071726 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7](Cl)[C:6]=2[CH:17]=1.[CH2:18]([O:20][CH2:21][CH2:22][CH2:23][Mg]Br)[CH3:19].Cl>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([CH2:23][CH2:22][CH2:21][O:20][CH2:18][CH3:19])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 202261183,5-Dichloro-5H-dibenzo[a,d]cyclohepteneHCID 178467821HCID 178467821, compound

Product 1

HCID 214120893-chloro-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3,5-Dichloro-5H-dibenzo[a,d]cycloheptene, dissolved in absolute ether, is added dropwise with stirring to a solution containing one equivalent of 3-ethoxypropylmagnesium bromide in ether. The mixture is stirred at room temperature for 1 hour, then at reflux for 2 hours. The mixture then is cooled, treated with dilute hydrochloric acid and the ether separated, washed with water and dried. The product is isolated by evaporation of the ether.

Workup

  1. additionis added dropwise
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. temperatureat reflux for 2 hours
  4. temperatureThe mixture then is cooled
  5. customthe ether separated
  6. washwashed with water
  7. customdried
  8. customThe product is isolated by evaporation of the ether

Sources & evidence

ORD record
ord-856ce9cc8b124689b8fb7b5896be80da
Source dataset
uspto-grants-1977_09
Patent number
US04048223

Reaction notes

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