Water → HCID 20388095, compound

HRID 427130Notes

Reaction equation

HRID 427130 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:18])[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]=[CH:13][C:7]=2[CH:6]=[C:5]([CH:19]([CH3:24])[C:20]([O:22]C)=[O:21])[CH:4]=1.[OH-].[Na+].O>O1CCCC1>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:18])[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]=[CH:13][C:7]=2[CH:6]=[C:5]([CH:19]([CH3:24])[C:20]([OH:22])=[O:21])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20388069HCID 20388069, compound

Product 1

HCID 20388095HCID 20388095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of step (a) is dissolved in tetrahydrofuran (10 ml) and 0.1 N aqueous sodium hydroxide (12 ml) is added. After 30 minutes the solution is added to water and washed with ether. The aqueous layer is acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The extract is dried, evaporated and the residue chromatographed on silica gel (10 g) eluting with hexane:ethyl acetate:acetic acid 60:40:2, to afford dl-2-(4-methoxy-5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)-propionic acid, mp 144°-147° (ethyl acetate-hexane).

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. customThe extract is dried
  4. customevaporated
  5. customthe residue chromatographed on silica gel (10 g)
  6. washeluting with hexane:ethyl acetate:acetic acid 60:40:2

Sources & evidence

ORD record
ord-0a5bd21933544da2bffe2617390e0e22
Source dataset
uspto-grants-1979_10
Patent number
US04172949

Reaction notes

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