Hydrochloric Acid → 4-(3'-Iso-propyl-4'-methoxyphenoxy)-3,5-dimethylbenzoic acid

HRID 2108619Notes

Reaction equation

HRID 2108619 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>CO>[CH:21]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[O:19][CH3:20])[O:12][C:11]1[C:2]([CH3:1])=[CH:3][C:4]([C:5]([OH:7])=[O:6])=[CH:9][C:10]=1[CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25150221HCID 25150221, compound

Product 1

HCID 183863804-(3'-Iso-propyl-4'-methoxyphenoxy)-3,5-dimethylbenzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzoate (8.53 g, 16.7 mmol, intermediate for the synthesis of Example 19-3) in methanol (60.0 mL) at 0° C. was added a solution of 1 N NaOH (28.15 mL, 28.15 mmol). The reaction mixture was stirred at room temperature for 16 h and acidified with cold concentrated HCl. The reaction mixture was extracted with ethyl acetate (10.0 mL) and the organic layer was dried over MgSO4. The solvent was removed under reduced pressure to afford 4-(3′-iso-propyl-4′-methoxyphenoxy)-3,5-dimethylbenzoic acid as a pink solid (1.38 g, 78%): 1H NMR (300 MHz, DMSO-d6): δ 12.88 (s, 1H), 7.76 (s, 2H), 6.85 (m, 1H), 6.75 (m, 1H), 6.34 (m, 1H), 3.73 (s, 3H), 3.20 (m, 1H), 2.11 (s, 6H), 1.12 (d, J=6.0 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (17:3); Rf=0.00.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (10.0 mL)
  2. dry with materialthe organic layer was dried over MgSO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a498eaffb37c4d429cc006efe71ef52b
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

Loading…