Sulfuric Acid → 5H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

HRID 972993Notes

Reaction equation

HRID 972993 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([C:6]1[CH:24]=[CH:23][C:9]2[C:10]3(OCC[O:19]3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH3:5].S(=O)(=O)(O)O>O>[CH:7]1[C:8]2[CH:14]=[CH:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10](=[O:19])[C:9]=2[CH:23]=[CH:24][C:6]=1[CH:4]([CH3:5])[C:3]([OH:25])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 537927402-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid methyl ester

Product 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-Yield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.0 Gm. of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid methyl ester is stirred in 25 ml. of 1:1 concentrated sulfuric acid:water for 12 hours. The mixture is poured into water and extracted with ethyl acetate and the extract is washed, dried and evaporated to afford a 70% yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid, m.p. (chloroform-hexane) 138°-139° C.; m.p. (acetone-hexane) 113°-115° C. Use of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid methyl ester gives a similar yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid, m.p. (acetone-hexane) 148°-149.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract is washed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-9e63cda70eb54c548768c6018106fee5
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

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