3,5-Dimethyl-4-(3'-isopropyl-4'-benzyloxyphenoxy)-nitrobenzene → 4-(4-Amino-2,6-dimethyl-phenoxy)-2-isopropyl-phenol

HRID 866018Notes

Reaction equation

HRID 866018 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:27]([O-])=O)[CH:5]=[C:6]([CH3:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[C:11]([CH:23]([CH3:25])[CH3:24])[CH:10]=1.[H][H]>C(O)C.O1CCCC1.C(OCC)(=O)C.CCCCCCC.[Pd]>[CH3:26][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([CH3:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:23]([CH3:24])[CH3:25])[CH:10]=1)[NH2:27]

Participants

7

Reactant 2

HCID 190300963,5-Dimethyl-4-(3'-isopropyl-4'-benzyloxyphenoxy)-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 121141794-(4-Amino-2,6-dimethyl-phenoxy)-2-isopropyl-phenol

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

3,5-Dimethyl-4-(3'-isopropyl-4'-benzyloxyphenoxy)-nitrobenzene, (2.86 kg, 7.31 mol) is dissolved in a mixture of ethanol/tetrahydrofuran (10:1, 114 L) and cooled to 100. This is admixed with 10% Pd/C (800 g) and the system is pressurized to 15 psi with hydrogen gas. The hydrogenation is continued for 18 hours. The mixture is then filtered through Celite and the Celite is washed with tetrahydrofuran (30 L). The filtrate is then evaporated in vacuo to dryness (50°, 3 Torr). The solid residue is triturated with heptane (3 L) and filtered. The after cake is washed with heptane (2×500 mL) to obtain crude product which is then dissolved in hot ethyl acetate (14 L) and diluted with heptane (30 L). The product slowly precipitates and the mixture is cooled at 10° for 1 hour, collected by filtration and washed with ethyl acetate/hexane 1:2 (2×500 mL). The filter cake is then dried (60°, 3 Torr) for 24 hours to yield 3,5-dimethyl-4-(3'-isopropyl-4'-hydroxyphenoxy)-aniline, m.p. 180°-181°.

Workup

  1. temperaturecooled to 100
  2. filtrationThe mixture is then filtered through Celite
  3. washthe Celite is washed with tetrahydrofuran (30 L)
  4. customThe filtrate is then evaporated in vacuo to dryness (50°, 3 Torr)
  5. customThe solid residue is triturated with heptane (3 L)
  6. filtrationfiltered
  7. washThe after cake is washed with heptane (2×500 mL)
  8. customto obtain crude product which
  9. customThe product slowly precipitates
  10. temperaturethe mixture is cooled at 10° for 1 hour
  11. filtrationcollected by filtration
  12. washwashed with ethyl acetate/hexane 1:2 (2×500 mL)
  13. customThe filter cake is then dried (60°, 3 Torr) for 24 hours

Sources & evidence

ORD record
ord-618921195d7b45039e1a2d5d604c63fe
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Reaction notes

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