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

HRID 1439417Notes

Reaction equation

HRID 1439417 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]=3[CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:16]([CH3:20])[C:17]([OH:19])=[O:18].[OH2:21].CCCCCC>C(O)(=O)C>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:21])[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:16]([CH3:20])[C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 962Water2×HCID 8058HexaneHCID 21397496HCID 21397496, compound

Product 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-Yield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1.10 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid is refluxed for 2 hours in 10 ml. of acetic acid and 7.5 ml. of water containing 2.24 gm. of ceric ammonium nitrate. The solution is poured into water and extracted with ethyl acetate. The extract is washed, dried and evaporated and the residue chromatographed on silica gel, eluting with 40:60:1 ethyl acetate:hexane:acetic acid, so as to isolate a 30% 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.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed
  3. customdried
  4. customevaporated
  5. customthe residue chromatographed on silica gel
  6. washeluting with 40:60:1 ethyl acetate

Sources & evidence

ORD record
ord-3487c29833944e51ba6fb4cb6234c6d2
Source dataset
uspto-grants-1977_11
Patent number
US04059611

Reaction notes

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