Sodium Hydroxide → 5-Iodo-2-methoxy-4-methylbenzoic acid

HRID 624308Notes

Reaction equation

HRID 624308 reaction equation
[I:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>C(O)C>[I:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 29934724Methyl 5-iodo-2-methoxy-4-methylbenzoate

Product 1

HCID 468293605-Iodo-2-methoxy-4-methylbenzoic acidYield 76.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 5-iodo-2-methoxy-4-methylbenzoate (3.0 g, 9.80 mmol) in ethanol (10 ml) in a 50 ml RB flask was added an aqueous solution of NaOH (0.784 g, 19.60 mmol, 1M). The reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum, the solid filtered and dried to give the titled compound (2.2 g, 74%). LCMS: (ES+) m/z=292 (M+H)+; Column. PUROSPHER@star RP-18 (4×55) mm, 3 μm; Buffer: 20 mM NH4OAc IN WATER; Mphase A: Buffer+MeCN (90+10); Mphase B: Buffer+MeCN (10+90); Flow: 2.5 ml/min Time (min.): 0 2 2.5 3; % B: 0 100 100 0; RT: 1.04 min.

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationthe solid filtered
  3. customdried

Sources & evidence

ORD record
ord-e27a0f9893b4462caed620253f2a30ad
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

Loading…