Acetic Acid → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal

HRID 1283677Notes

Reaction equation

HRID 1283677 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.O.N(C(NC1C=CC=CC=1)C)C1C=CC=CC=1.C(O)(=O)C>COCCOCCOC.CO>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[CH:14]=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 15852811DianilinoethaneHCID 203106912-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride

Product 1

HCID 214093832-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8150DiglymeSolvent2×

Procedure

0.25 G. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)-propionyl chloride (as prepared in Preparation 10 above) is dissolved in 4 ml. of diglyme and the solution cooled to -78°C. 3.5 Ml. of 0.045 molar lithium aluminum tri-tertiary butoxy hydride in diglyme is added, in 0.5 ml. portions over the course of 1 hour, to this solution. The mixture is warmed to room temperature and poured into water and extracted with ether. The extract is washed, dried and evaporated to give a crude product to which is added a solution of 0.106 g. of dianilinoethane and 0.072 g. of acetic acid in 5 ml. of methanol. The mixture is left for 1 hour than decanted from the insoluble product, α-(1,3-diphenyl-2-imidazolidinyl) 2-ethyl-5-oxo-5H-dibenzo[a,d]cycloheptene [a gum; nmr spectrum in deuterochloroform relative to tetramethylsilane: 1.47 (doublet, CHCH3), 5.77 (singlet, N-CH-N) acid 6.90 ppm (singlet, 10H, 11H). This compound is dissolved in 10 ml. of ether and the solution shaken with dilute hydrochloric acid. The ethereal layer is dried and evaporated to give 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal [a gum; nmr spectrum in deuterochloroform relative to tetramethylsilane: 0.98 (doublet, CHCH3), 3.78 (quartet, CHCH3), 7.02 (singlet, 10H, 11H) and 9.72 ppm (doublet, CHO); mass spectrum: 262 (M+) 233, 205] .

Workup

  1. customover the course of 1 hour
  2. extractionextracted with ether
  3. washThe extract is washed
  4. customdried
  5. customevaporated
  6. customto give a crude product to which
  7. additionis added a solution of 0.106 g
  8. customthan decanted from the insoluble product, α-(1,3-diphenyl-2-imidazolidinyl) 2-ethyl-5-oxo-5H-dibenzo[a,d]cycloheptene [a gum
  9. dissolutionThis compound is dissolved in 10 ml
  10. customThe ethereal layer is dried
  11. customevaporated

Sources & evidence

ORD record
ord-f53dbed02c7c49e79c130b6b9480a3d6
Source dataset
uspto-grants-1976_08
Patent number
US03975540

Reaction notes

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