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

HRID 1486180Notes

Reaction equation

HRID 1486180 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-793ab56df13b4ab2b4fad41eb28c690d
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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