Hydrochloric Acid → 3-(1-Hexenyl)-4-methoxybenzoic acid

HRID 850437Notes

Reaction equation

HRID 850437 reaction equation
Cl.[CH:2]([C:8]1[CH:9]=[C:10]([C:16]2[O:17]CC(C)(C)N=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15])=[CH:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cl-].[Na+].[OH2:25]>>[CH:2]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:16]([OH:17])=[O:25])=[CH:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 541623052-[3-(1-Hexenyl)-4-methoxyphenyl]-4,4-dimethyl-4,5-dihydrooxazoleHCID 57417360Sodium chloride; water

Product 1

HCID 538972933-(1-Hexenyl)-4-methoxybenzoic acidYield 35%

Procedure

6N Hydrochloric acid (20 ml) was added to 2-[3-(1-hexenyl)-4-methoxyphenyl]-4,4-dimethyl-4,5-dihydrooxazole (583 mg, 2.03 mmol), and the mixture was refluxed under heating for 4 hours. Saturated saturated brine (30 ml) was added to this solution, and the aqueous layer was extracted 3 times with ethyl acetate (50 ml). The organic layers were combined, and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=2/1) to give 3-(1-hexenyl)-4-methoxybenzoic acid (164.3 mg, 35%) as a mixture (colorless crystals) of geometrical isomers (1:1).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. extractionthe aqueous layer was extracted 3 times with ethyl acetate (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-9f684d286cd446c085c4a4266305f44a
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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