Hydrochloric Acid → HCID 54514974, compound

HRID 2163638Notes

Reaction equation

HRID 2163638 reaction equation
[CH3:1][C:2]1([C:7]2[C:17]3[CH2:16][CH2:15][C:14]4[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=4[C:12]([CH2:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])(O)[C:11]=3[CH:10]=[CH:9][CH:8]=2)OCC[O:3]1.Cl>C(O)C>[C:2]([C:7]1[C:17]2[CH2:16][CH2:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[C:12](=[CH:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22750664HCID 22750664, compound

Product 1

HCID 54514974HCID 54514974, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.8 g. of 1-(2-methyl-1,3-dioxolan-2-yl)-10,11-dihydro-5-(3-dimethylaminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene are heated with 50 ml. of ethanol and 6 ml. of 25% ethanolic hydrochloric acid over a 21/2 hour period at reflux. Thereafter, the reaction mixture is concentrated under vacuum, dissolved in water, make alkaline with dilute sodium hydroxide and extracted with ether. The extract is washed with water, dried with sodium sulfate, filtered and evaporated whereby there is obtained 1-acetyl-10,11-dihydro-5-(3-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene as a yellow oil, whose NMR and IR spectrum are in agreement with their constitution. Through mass chromatography, it is determined that the product is a mixture of the geometric isomers α (30%) and β (70%).

Workup

  1. concentrationThereafter, the reaction mixture is concentrated under vacuum
  2. dissolutiondissolved in water
  3. extractionextracted with ether
  4. washThe extract is washed with water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated whereby there

Sources & evidence

ORD record
ord-ad53e57c4a06414eabe2634a8d4c2f89
Source dataset
uspto-grants-1979_01
Patent number
US04136116

Reaction notes

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