Water → (5-Hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

HRID 132988Notes

Reaction equation

HRID 132988 reaction equation
[OH:1][CH2:2][C:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([OH:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].O>O1CCCC1>[C:25]([O:1][CH2:2][C:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([OH:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 586468421-(Hydroxymethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

Product 1

HCID 58646846(5-Hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 g of 1-(hydroxymethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol prepared in Example 1-c was dissolved in 20 ml of tetrahydrofuran, and 1.2 ml of pyridine and 1.4 ml of acetic anhydride were added at room temperature, followed by stirring for 3 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate for two times. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:9), to give 3.5 g of the title compound as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate for two times
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-bb7e811a05c64370bb1f6f0dc9c8b146
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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