2-(4-Chloro-3-nitrophenylcarboxy)ethyl 3,5-di-t-butyl-4-hydroxybenzoate → 2-(3-Amino-4-chlorophenylcarboxy)ethyl 3,5-di-t-butyl-4-hydroxybenzoate

HRID 845366Notes

Reaction equation

HRID 845366 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:26]=[C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:28]=1[OH:29])[C:8]([O:10][CH2:11][CH2:12][C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([N+:23]([O-])=O)[CH:17]=1)=[O:14])=[O:9])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.O.[Fe]>[C:30]([C:27]1[CH:26]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:28]=1[OH:29])[C:8]([O:10][CH2:11][CH2:12][C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([NH2:23])[CH:17]=1)=[O:14])=[O:9])([CH3:32])([CH3:33])[CH3:31]

Participants

5

Reactant 1

HCID 201310052-(4-Chloro-3-nitrophenylcarboxy)ethyl 3,5-di-t-butyl-4-hydroxybenzoate

Product 1

HCID 201310072-(3-Amino-4-chlorophenylcarboxy)ethyl 3,5-di-t-butyl-4-hydroxybenzoateYield 93%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Iron metal powder (13.4 g, 0.24 mole) was added portionwise to a solution of the nitro compound (22.9 g, 0.048 mole) from (b) in acetic acid (110 ml) and water (10 ml), heated on a steam bath. Heating was continued for a further 3 hours, after which the suspension was filtered hot through kieselguhr. The filtrate was poured into a mixture of ice/water (1 liter) with rapid stirring and the precipitate was collected by filtration to give the product as a white solid (20 g, 93%). m.p. 122°-124° C.

Workup

  1. temperatureheated on a steam bath
  2. temperatureHeating
  3. filtrationafter which the suspension was filtered hot through kieselguhr
  4. additionThe filtrate was poured into a mixture of ice/water (1 liter)
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c00da7991c2344519e3e7dc5e18e97e5
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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