Hydrochloric Acid → 3-Amino-4-chlorophenyl 3,5-di-t-butyl-4-hydroxybenzoate

HRID 845363Notes

Reaction equation

HRID 845363 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[C:8]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([N+:19]([O-])=O)[CH:13]=1)=[O:10])([CH3:5])([CH3:4])[CH3:3].O1CCCC1>[Fe].O>[C:2]([C:6]1[CH:7]=[C:8]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([NH2:19])[CH:13]=1)=[O:10])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 201310134-Chloro-3-nitrophenyl 3,5-di-t-butyl-4-hydroxybenzoate

Product 1

HCID 201310123-Amino-4-chlorophenyl 3,5-di-t-butyl-4-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Iron metal powder (50.2 g; 0.897 mole) and 10M-hydrochloric acid (92 ml; 0.92 mole) were added alternatively over 11/2 hr. to a mixture, of the nitro compound (60.6 g; 0.149 mole) from (a), tetrahydrofuran (520 ml) and water (52 ml), heated under reflux. Heating was continued for a further 31/2 hr. after which the mixture was filtered. The filtrate was evaporated to dryness and the residue partitioned between toluene (500 ml) and water (400 ml). The layers were separated and the toluene solution filtered through kieselguhr, dried and evaporated to give a solid. This material was crystallized from methanol (100 ml) to give the product (41 g; 75%) as a white solid, m.p. 64°-66° C.

Workup

  1. temperatureunder reflux
  2. temperatureHeating
  3. custom2 hr
  4. filtrationafter which the mixture was filtered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue partitioned between toluene (500 ml) and water (400 ml)
  7. customThe layers were separated
  8. filtrationthe toluene solution filtered through kieselguhr
  9. customdried
  10. customevaporated
  11. customto give a solid
  12. customThis material was crystallized from methanol (100 ml)
  13. customto give the product (41 g; 75%) as a white solid, m.p. 64°-66° C.

Sources & evidence

ORD record
ord-16581919a2074362802558cd6b09ba66
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

Loading…