Sodium Hydroxide → 3-Methyl-2-(2-oxazolyl)benzoic acid

HRID 64210Notes

Reaction equation

HRID 64210 reaction equation
[CH3:1][C:2]1[C:3]([C:13]2[O:14][CH:15]=[CH:16][N:17]=2)=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>CO>[CH3:1][C:2]1[C:3]([C:13]2[O:14][CH:15]=[CH:16][N:17]=2)=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90412267Ethyl 3-methyl-2-(oxazol-2-yl)benzoate

Product 1

HCID 904118273-Methyl-2-(2-oxazolyl)benzoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the title compound of step A (166 mg, 0.72 mmol) was added MeOH (7.2 mL) and 1M NaOH(aq) (7.2 mL). MeOH was evaporated and then 1 M HCl(aq) was added. To the solution was added DCM and the aqueous was extracted with DCM (3×). The combined organic layers were dried over MgSO4, filtered and evaporated to give the title compound (145 mg). MS (ESI) mass calcd. for C11H9NO3, 203.1. m/z found 204.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.20 (s, 1H), 7.79-7.68 (m, 1H), 7.65-7.49 (m, 2H), 7.35 (s, 1H), 4.34 (s, 1H), 2.20 (s, 3H).

Workup

  1. customMeOH was evaporated
  2. addition1 M HCl(aq) was added
  3. additionTo the solution was added DCM
  4. extractionthe aqueous was extracted with DCM (3×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e2dd0d69487f4684848b9b7c669735f8
Source dataset
uspto-grants-2016_09
Patent number
US09447117B2

Reaction notes

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