1-Butanol → HCID 15430965, compound

HRID 482852Notes

Reaction equation

HRID 482852 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)[CH:8]=1)([O-])=O.C(O)CCC.[H][H]>[Pd].C(N(CC)CC)C>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:23]=[CH:24][CH:25]=[CH:26][C:4]=2[NH2:1])[CH:8]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 3095746HCID 3095746, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15430965HCID 15430965, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 145.3 g of 1,3-bis(2-nitrophenoxy)benzene, 340 mL of butanol, 9 mL of triethylamine, and 1.7 g of 5% palladium on carbon was heated to 70° C. in a 1.0 liter stainless steel stirred autoclave and pressurized with hydrogen to 4.1 MPa. This pressure was maintained for 1 hour after the hydrogen uptake had ceased. The autoclave was cooled to room temperature and discharged. The product slurry redissolved on reheating; the solution was filtered through diatomaceous earth to remove the catalyst, cooled to room temperature, and the product precipitated with hexane. The precipitated product was recovered by filtration and vacuum dried at 70° C. The yield of 1,3-bis(2-aminophenoxy)benzene was 95.2 g (79%).

Workup

  1. dissolutionThe product slurry redissolved
  2. filtrationthe solution was filtered through diatomaceous earth
  3. customto remove the catalyst
  4. temperaturecooled to room temperature
  5. customthe product precipitated with hexane
  6. filtrationThe precipitated product was recovered by filtration and vacuum
  7. customdried at 70° C

Sources & evidence

ORD record
ord-a99f19402e68499ba1320977354a81de
Source dataset
uspto-grants-1986_03
Patent number
US04576857

Reaction notes

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