Sodium Hydroxide → 3-Cyano-5-isopropoxybenzoic acid

HRID 1809516Notes

Reaction equation

HRID 1809516 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH:14]([CH3:16])[CH3:15])[CH:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[Na+]>CCO.Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH:14]([CH3:16])[CH3:15])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67195394Methyl 3-cyano-5-isopropoxybenzoate

Product 1

HCID 671962143-Cyano-5-isopropoxybenzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of methyl 3-cyano-5-isopropoxybenzoate (1.19 g, 5.4 mmol) in EtOH (4 mL) was added 5N NaOH (3 mL, 15 mmol). After stirring at room temperature for 4 h, the reaction mixture was diluted with 1N HCl and extracted with EA. The combined organic layers were dried over Na2SO4 and concentrated to provide 920 mg (83%) of 3-cyano-5-isopropoxybenzoic acid as a white solid. LCMS-ESI (m/z) calculated for C11H11NO3: 205.2; found 206.1 [M+H]+, tR=2.97 min. 1H NMR (400 MHz, CDCl3) δ 7.93 (t, J=1.4 Hz, 1H), 7.80 (dd, J=2.6, 1.4 Hz, 1H), 7.35 (dd, J=2.6, 1.4 Hz, 1H), 4.71-4.56 (m, 1H), 1.38 (dd, J=6.1, 2.2 Hz, 6H).

Workup

  1. extractionextracted with EA
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6ff5ef69705e4239a830263ae5ce1575
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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