Hydrochloric Acid → 6-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-ylmethanol

HRID 132995Notes

Reaction equation

HRID 132995 reaction equation
C([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[C:20]([I:21])[C:12]=3[C:11](=[O:22])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=O)C.C(OCC1C2CCC3C=CC=CC=3C(=O)C=2C(I)=CC=1)(=O)C.O.Cl>O1CCCC1.CO.[OH-].[Na+]>[I:21][C:20]1[C:12]2[C:11](=[O:22])[C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([CH2:5][OH:4])[C:16]=3[CH2:15][CH2:14][C:13]=2[CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12150903(6-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetateHCID 12150904(4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Product 1

HCID 586468506-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-ylmethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.5 g of the mixture of (6-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate and (4-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate prepared in Example 1-g was dissolved in a mixed solvent of 5 ml of tetrahydrofuran and 5 ml of methanol, and 0.1 ml of 5N sodium hydroxide solution was added at room temperature, followed by stirring at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was neutralized with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 1.3 g of a mixture of the title compound with a 4-iodo form as a colorless powder.

Workup

  1. additionwas added at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0bca8ded1dd44dc7837963c396463a27
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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