1-[2,6-Bisbenzyloxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone → 1-[6-Benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone

HRID 1766662Notes

Reaction equation

HRID 1766662 reaction equation
C([O:8][C:9]1[C:14]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]3[C:17]=2[CH2:18][CH2:19][CH2:20]3)=[CH:13][CH:12]=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:10]=1[C:37](=[O:39])[CH3:38])C1C=CC=CC=1.FC(F)(F)C(O)=O.O.CSC>ClCCl>[CH2:30]([O:29][C:11]1[C:10]([C:37](=[O:39])[CH3:38])=[C:9]([OH:8])[C:14]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]3[C:17]=2[CH2:18][CH2:19][CH2:20]3)=[CH:13][CH:12]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 211105561-[2,6-Bisbenzyloxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanoneHCID 86597598Trifluoroacetic acid water dimethylsulfide

Product 1

HCID 211105611-[6-Benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanoneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2,6-bisbenzyloxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone (10.6 g) in dichloromethane (15 mL) was added a mixed solvent of trifluoroacetic acid/water/dimethylsulfide (7/3/1) (30 mL), and the mixture was stirred at room temperature for 12 hours. Adding water, the reaction mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium hydrogen carbonate until the aqueous layer became weak alkaline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was crystallized from ethyl acetate and hexane to give the title compound (8.07 g).

Workup

  1. extractionAdding water, the reaction mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-c955212839704d09a6a6121a9717bc9a
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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