Potassium Hydroxide → 5-Isopropyl-2,4-dimethoxybenzoic acid

HRID 389955Notes

Reaction equation

HRID 389955 reaction equation
[OH-].[K+].[CH:3]([C:6]1[C:7]([O:18][CH3:19])=[CH:8][C:9]([O:16][CH3:17])=[C:10]([CH:15]=1)[C:11]([O:13]C)=[O:12])([CH3:5])[CH3:4]>CO.O>[CH:3]([C:6]1[C:7]([O:18][CH3:19])=[CH:8][C:9]([O:16][CH3:17])=[C:10]([CH:15]=1)[C:11]([OH:13])=[O:12])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59263169Methyl 5-isopropyl-2,4-dimethoxybenzoate

Product 1

HCID 534150805-Isopropyl-2,4-dimethoxybenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous potassium hydroxide (50% w/v, 0.2 ml) was added to a suspension of methyl 5-isopropyl-2,4-dimethoxybenzoate (330 mg, 1.39 mmol) in methanol (5 ml) and water (2 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The organic material was extracted with ethyl acetate (2×30 ml) and the combined organic extracts were evaporated in vacuo to afford 5-isopropyl-2,4-dimethoxybenzoic acid (305 mg, 98%) as an off-white solid. 1H NMR (DMSO-d6) 12.07 (1H, br s), 7.57 (1H, s), 6.64 (1H, s), 3.90 (3H, s), 3.85 (3H, s), 3.13 (1H, m), 1.14 (6H, d). MS: [M+H]+ 225.

Workup

  1. temperatureat reflux for 3 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (10 ml)
  4. extractionThe organic material was extracted with ethyl acetate (2×30 ml)
  5. customthe combined organic extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-8307d9d68e854540bbdb2ee199c44c52
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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