Hydrochloric Acid → 5-Isopropyl-2,4-dimethoxybenzoic acid

HRID 41446Notes

Reaction equation

HRID 41446 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[C:7]([O:13][CH3:14])=[CH:6][C:5]=1[O:15][CH3:16].[OH-].[Na+].Cl>C1COCC1.O.CCOC(C)=O>[CH:10]([C:8]1[C:7]([O:13][CH3:14])=[CH:6][C:5]([O:15][CH3:16])=[C:4]([CH:9]=1)[C:3]([OH:17])=[O:2])([CH3:12])[CH3:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59263169Methyl 5-isopropyl-2,4-dimethoxybenzoate

Product 1

HCID 534150805-Isopropyl-2,4-dimethoxybenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Isopropyl-2,4-dimethoxy-benzoic acid methyl ester (5.5 g, 23.1 mmol) and NaOH (1.38 g, 34.6 mmol) in THF (46 ml) and water (46 ml) was warmed to 50° C. overnight. The reaction was cooled and diluted with water and EtOAc. The aqueous layer was neutralised with HCl (1N, aq.). The product was extracted with EtOAc (×3) and the combined organic layers were washed with brine and dried over MgSO4. The product was filtered and evaporated to dryness to yield 5-isopropyl-2,4-dimethoxy-benzoic acid as a pale peach solid (4.7 g). 1H NMR (DMSO-d6) 12.1 (1H, br s), 7.62 (1H, s), 6.71 (1H, s), 3.95 (3H, s), 3.91 (3H, s), 3.19 (1H, sept), 1.18 (6H, d). MS: [M+H]+ 225.

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe product was extracted with EtOAc (×3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe product was filtered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-3cdce4123a7b4346ba6d9b813835462e
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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