Hydrochloric Acid → HCID 10171341, compound

HRID 1077682Notes

Reaction equation

HRID 1077682 reaction equation
[CH2:1]([O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:17][OH:18].C[O-].[Na+].Cl>CO>[CH2:1]([O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([NH:17][OH:18])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 4226083methyl 4-butoxybenzoate2×HCID 10942334Sodium Methoxide

Product 1

HCID 10171341HCID 10171341, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Compound HA-3 (4-Butoxybenzohydroxamic Acid) was synthesised from methyl 4-butoxybenzoate. Hydroxylamine hydrochloride (6.95 g, 100 mmol) was dissolved in AR Grade methanol (20 mL) under Argon, then added to NaOMe (25% w/w in MeOH) 52.9 mL, 231 mmol) under Ar with ice cooling. A solution of methyl 4-butoxybenzoate (10.0 g, 48.0 mmol) in MeOH (50 mL) was then added, and the reaction stirred at room temperature under Ar. After 3 weeks, the reaction mixture was acidified to pH 6 with conc. HCl (caution!). The mixture was filtered and the filtrate evaporated to give a precipitate. This was extracted with CHCl3, the combined extracts dried (MgSO4) and the solvent evaporated. The residue was recrystallised from EtOH to give 4-butoxybenzohydroxamic acid as crystals, m.p. 152.6°-152.9° C. (8.25 g, 82%).

Workup

  1. waitAfter 3 weeks
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customto give a precipitate
  5. extractionThis was extracted with CHCl3
  6. dry with materialthe combined extracts dried (MgSO4)
  7. customthe solvent evaporated
  8. customThe residue was recrystallised from EtOH

Sources & evidence

ORD record
ord-1ce49a00ab8e4b278681a99aaf8388b6
Source dataset
uspto-grants-1996_08
Patent number
US05545507

Reaction notes

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