Methanol → 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester

HRID 972986Notes

Reaction equation

HRID 972986 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3C(=O)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:17]([CH3:20])[C:18]#N.[OH2:21].[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:33][OH:34].[OH2:35]>CCOCC>[CH3:22][O:21][C:18](=[O:35])[CH:17]([C:2]1[CH:3]=[CH:4][C:5]2[C:33](=[O:34])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:7][C:8]=3[CH:9]=[CH:10][C:11]=2[CH:1]=1)[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 214030952-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionitrile

Product 1

HCID 123988252-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.29 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionitrile and 0.85 gm. of p-toluenesulfonic acid monohydrate are refluxed for 6 hours in 25 ml. of methanol. The solution is cooled and added to water and ether. The ethereal solution is washed, dried and evaporated to give a 75% yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester as an oil which slowly crystallized, m.p. 37°-39° C., NMR: δCDCl3 1.55(d), 3.67(s), 3.83(g), 7.04(s) ppm. Use of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetonitrile gives a similar yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid methyl ester, m.p. 67°-69° C.

Workup

  1. temperatureThe solution is cooled
  2. washThe ethereal solution is washed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-b2466c35b43b4602abddbb0394728eaa
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

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