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

HRID 2072517Notes

Reaction equation

HRID 2072517 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 then 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. customthen 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-98bf4c3036794d51a33a06e881c60c5c
Source dataset
uspto-grants-1977_09
Patent number
US04051260

Reaction notes

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