2,3-Dimethyl-2-butene → 3-Iodo-2-methoxybenzoic acid

HRID 1404367Notes

Reaction equation

HRID 1404367 reaction equation
[I:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].CC(=C(C)C)C.O.P([O-])([O-])(O)=[O:20].[Na+].[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[I:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([OH:20])=[O:6]

Participants

8

Reactant 4

HCID 112502,3-Dimethyl-2-buteneHCID 61488Phosphoric acid, disodium salt, hydrateHCID 108014193-Iodo-2-methoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 121684323-Iodo-2-methoxybenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-iodo-2-methoxy-benzaldehyde (3.68 g, 14 mmol) in tert-butanol (70 mL) was added 2,3-dimethyl-but-2-ene (7 mL) followed by a solution comprising disodium hydrogen phosphate monohydrate (7.56 g 56 mmol) and sodium chlorite (7.56 g, approx. 66 mmol, technical grade) in water (70 mL). The resulting mixture was stirred for 20 minutes then diluted with ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated. The residual solid was recrystallized from cyclohexane to give the title compound as a white solid.

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residual solid was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-a19eff3b75704970b2ba4dcdcd387faf
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

Loading…