7-(2-Chloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuran → HCID 13246036, compound

HRID 2295796Notes

Reaction equation

HRID 2295796 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:20]([O-])=O)[CH:5]=[CH:6][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:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][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)[NH2:20]

Participants

5

Reactant 2

HCID 132459937-(2-Chloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuranHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13246036HCID 13246036, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

To a solution containing 42.5 g of 3-chloro-4-(2,3-dihydro-2,2-dimethyl-7-benzofuranyloxy)-1-nitrobenzene in 600 ml of toluene was added 1.5 g of 5% Pt on carbon. This mixture was then placed in a 1 L rocking hydrogenator. An atmosphere of hydrogen at 100 psi was introduced into the bomb. The pressure was maintained between 100 psi and 80 psi until the hydrogen uptake ceased. The contents were removed from the bomb and filtered through celite. Removal of the solvents from the filtrates afforded 34.91 g of white solid, mp 102°-104° C. NMR (CDCl3) δ1.45 (s, 6H), 3.0 (s, 2H), 3.55 (broad s, 2H), 6.2-6.9 (m, 6H).

Workup

  1. customThe contents were removed from the bomb
  2. filtrationfiltered through celite
  3. customRemoval of the solvents from the filtrates

Sources & evidence

ORD record
ord-6f1508d4105542a19f36372c8e9c2cb8
Source dataset
uspto-grants-1984_01
Patent number
US04426385

Reaction notes

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