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

HRID 1576184Notes

Reaction equation

HRID 1576184 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 six 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: δCDCl 3 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-83557f49890e4bef8639afce751c1a64
Source dataset
uspto-grants-1976_09
Patent number
US03979430

Reaction notes

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