7-(2,6-Dichloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuran → HCID 13246037, compound

HRID 978479Notes

Reaction equation

HRID 978479 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:21]([O-])=O)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[C:17]2[O:16][C:15]([CH3:19])([CH3:18])[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.[H][H]>C1(C)C=CC=CC=1.[Pt]>[Cl:20][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([Cl:1])[C:7]=1[O:8][C:9]1[C:17]2[O:16][C:15]([CH3:18])([CH3:19])[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)[NH2:21]

Participants

5

Reactant 2

HCID 132459927-(2,6-Dichloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 13246037HCID 13246037, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 29.2 g of 3,5-dichloro-4-(2,3-dihydro-2,2-dimethyl-7-benzofuranyloxy)-1-nitrobenzene in 500 ml of toluene was added 2.3 g of 5% platinum on carbon catalyst. This mixture was then charged into a 1 L rocking Parr reactor. The reactor was purged twice with nitrogen then twice with hydrogen, then finally filled with hydrogen to a pressure of 100 psig. The hydrogen pressure was maintained between 75 and 100 psig during the course of the reaction. After hydrogen uptake ceased, the reaction mixture was removed from the reactor. This was filtered through celite. Removal of the solvents afforded 23.95 g of off-white crystals. mp 140°-145° C. NMR (CDCl3): 1.53 (s, 6H), 3.03 (s, 2H), 3.70 (broad s, 2H), 6.2-7.0 (M, 5H, contains singlet at 6.62).

Workup

  1. additionThis mixture was then charged into a 1 L
  2. customThe reactor was purged twice with nitrogen
  3. additiontwice with hydrogen, then finally filled with hydrogen to a pressure of 100 psig
  4. temperatureThe hydrogen pressure was maintained between 75 and 100 psig
  5. customduring the course of the reaction
  6. customthe reaction mixture was removed from the reactor
  7. filtrationThis was filtered through celite
  8. customRemoval of the solvents

Sources & evidence

ORD record
ord-1132b06db1084be1827617c6f9096f9a
Source dataset
uspto-grants-1987_05
Patent number
US04665097

Reaction notes

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