Hydrochloric Acid → HCID 19079062, compound

HRID 1735851Notes

Reaction equation

HRID 1735851 reaction equation
[CH2:1]([C:4]1([CH:19]=[CH:20][O:21]C2CCCCO2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([C:4]1([CH2:19][CH:20]=[O:21])[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67604664HCID 67604664, compound

Product 1

HCID 19079062HCID 19079062, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolved 10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl-(2-tetrahydropyranyloxy-ethene) (4.82 g, 13.37 mmol) in 50 mL of THF. Added 50 mL of 0.2N HCl, and refluxed for 18 hours. Cooled to room temperature, and added 150 mL of saturated NaHCO3. Extracted with ethyl acetate. Washed combined organic extracts with saturated NaCl, dried (MgSO4), filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane. Combined appropriate fractions and evaporated to give 3.32 g (90% yield) of 2-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-ethanal).

Workup

  1. temperaturerefluxed for 18 hours
  2. extractionExtracted with ethyl acetate
  3. washWashed
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurified crude product by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane
  8. customevaporated

Sources & evidence

ORD record
ord-2cee9db2f3214dbfbc9555321598ddf7
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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