Hydrochloric Acid → HCID 54514974, compound

HRID 1606128Notes

Reaction equation

HRID 1606128 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, made 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-f3c364b619a44df5af870441be26da29
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

Loading…