2-Methyl-2-butene → 3-(1,1-Dimethylheptyl)-4-methoxybenzoic acid

HRID 850417Notes

Reaction equation

HRID 850417 reaction equation
[CH3:1][C:2]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH:13]=[O:14])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CC(=CC)C.Cl([O-])=[O:26].[Na+].P([O-])(O)(O)=O.[Na+].[OH-].[Na+]>O.C(O)(C)(C)C>[CH3:9][C:2]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:13]([OH:26])=[O:14])([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 5

HCID 105532-Methyl-2-buteneHCID 14798Sodium HydroxideHCID 193633883-(1,1-Dimethylheptyl)-4-methoxybenzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 193633733-(1,1-Dimethylheptyl)-4-methoxybenzoic acidYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

3-(1,1-Dimethylheptyl)-4-methoxybenzaldehyde (13 g, 49.5 mmol), t-butanol (65 ml) and 2-methyl-2-butene (35.2 ml, 332 mmol) were mixed, and to this solution was added dropwise a solution prepared by mixing sodium chlorite (7.37 g, 64.4 mmol), sodium dihydrogenphosphate (7.73 g, 64.4 mmol) and water (50 ml). The mixture was stirred at room temperature for 12 hours. A 1N sodium hydroxide solution (100 ml) was added, and t-butanol was evaporated under reduced pressure. Conc. hydrochloric acid was added to make the mixture acidic. The aqueous layer was extracted 3 times with ethyl acetate (150 ml). The organic layers were combined, washed with saturated brine (100 ml), 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 (n-hexane/ethyl acetate=5/1-2/1) to give 3-(1,1-dimethylheptyl)-4-methoxybenzoic acid (10.7 g, 77%) as colorless crystals.

Workup

  1. additionto this solution was added dropwise a solution
  2. customprepared
  3. customt-butanol was evaporated under reduced pressure
  4. additionConc. hydrochloric acid was added
  5. extractionThe aqueous layer was extracted 3 times with ethyl acetate (150 ml)
  6. washwashed with saturated brine (100 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate=5/1-2/1)

Sources & evidence

ORD record
ord-aa2ff9ad690b4eeabcf75021aa132123
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

Loading…