Acetic Acid → HCID 11031370, compound

HRID 2299647Notes

Reaction equation

HRID 2299647 reaction equation
C(OC(=O)[CH2:7][CH2:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]([O:17][CH3:18])[C:10]=1[CH2:19][CH2:20][C:21]([O:23]C(C)(C)C)=O)(C)(C)C.[H-].[Na+].C(O)(=O)C>C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH3:18][O:17][C:11]1[C:10]2[CH2:19][CH2:20][C:21](=[O:23])[CH2:7][CH2:8][C:9]=2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 53985092HCID 53985092, compound

Product 1

HCID 11031370HCID 11031370, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

3-[2-(2-tert-butoxycarbonylethyl)-3,6-dimethoxyphenyl]-propionic acid tert-butyl ester (6.33 g) was added dropwise to a refluxed solution of sodium hydride (578 mg) in dry toluene (60 ml) and dry tert-butyl alcohol (0.5 ml), and stirred for 3 hours. After cooling, to the reaction mixture glacial acetic acid was added dropwise followed by addition of ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. To the residue were added methanol (50 ml) and 6N hydrochloric acid (15 ml), and this mixture was refluxed for 3 hours, poured into ice and extracted with ethyl acetate. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford 1,4-dimethoxy-5,6,8,9-tetrahydrobenzocyclohepten-7-one (2.99 g).

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. additionTo the residue were added methanol (50 ml) and 6N hydrochloric acid (15 ml)
  7. temperaturethis mixture was refluxed for 3 hours
  8. additionpoured into ice
  9. extractionextracted with ethyl acetate
  10. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-3cb39acc72c8405093d1b313287bc799
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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