Potassium Hydroxide → HCID 58236451, compound

HRID 389966Notes

Reaction equation

HRID 389966 reaction equation
[OH:1][C:2]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:15][CH2:16][O:17][CH3:18])[CH:3]=1.[OH-].[K+]>CO.O>[OH:1][C:2]1[C:11]([CH:12]([CH3:13])[CH3:14])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:15][CH2:16][O:17][CH3:18])[CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58236469Methyl 4-hydroxy-5-isopropyl-2-(methoxymethyloxy)benzoate

Product 1

HCID 58236451HCID 58236451, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The crude methyl 4-hydroxy-5-isopropyl-2-(methoxymethyloxy)benzoate was dissolved in methanol (20 ml) and water (8 ml), aqueous potassium hydroxide (50% w/v, 5 ml) was added and the mixture was stirred and held at reflux for 16 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (30 ml). The organic material was extracted with ethyl acetate (2×20 ml) and the combined organic extracts were evaporated in vacuo to afford a yellow oil that was subjected to column chromatography on a Strata-NH2 cartridge. Elution with 2M ammonia in methanol afforded crude 4-hydroxy-5-isopropyl-2-(methoxymethyloxy)benzoic acid (180 mg, 25%) as a pale grey solid that was used without further purification. MS: [M+Na]+ 263.

Workup

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (30 ml)
  4. extractionThe organic material was extracted with ethyl acetate (2×20 ml)
  5. customthe combined organic extracts were evaporated in vacuo
  6. customto afford a yellow oil that
  7. washElution with 2M ammonia in methanol

Sources & evidence

ORD record
ord-6a64d750005b4a56a18d9427a742a28b
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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