Potassium Hydroxide → 2-Nitro-5-(3-thienylmethoxy)phenol

HRID 322949Notes

Reaction equation

HRID 322949 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[OH-:18].[K+]>C(O)(C)(C)C>[N+:15]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)=[CH:7][C:2]=1[OH:18])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 220101462-Fluoro-4-(3-thienylmethoxy)nitrobenzene

Product 1

HCID 220103422-Nitro-5-(3-thienylmethoxy)phenol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 2-fluoro-4-(3-thienylmethoxy)nitrobenzene (4.21 g), aqueous potassium hydroxide solution (50 mL; 50% w/v) and t-butanol (20 mL) is heated at reflux for 4 hours. It is then evaporated to dryness and the residue is partitioned between ethyl acetate (100 mL) and hydrochloric acid (100 mL; 1 N). The organic phase is washed with water (3×100 mL), dried over magnesium sulphate, filtered and evaporated, to give 2-nitro-5-(3-thienylmethoxy)phenol, in the form of a yellow solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. customIt is then evaporated to dryness
  4. customthe residue is partitioned between ethyl acetate (100 mL) and hydrochloric acid (100 mL; 1 N)
  5. washThe organic phase is washed with water (3×100 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-90c13fef15b74e0bbc01c05a818beff2
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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