2-Methyl-2-butene → HCID 19363375, compound

HRID 850423Notes

Reaction equation

HRID 850423 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[CH:18]=[O:19].CC(=CC)C.Cl([O-])=[O:26].[Na+].P([O-])(O)(O)=O.[Na+].[OH-].[Na+]>O.C(O)(C)(C)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[C:18]([OH:26])=[O:19]

Participants

8

Reactant 5

HCID 105532-Methyl-2-buteneHCID 14798Sodium HydroxideHCID 19363267HCID 19363267, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 19363375HCID 19363375, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

1-Bromo-4-pentyloxynaphthalene-2-carbaldehyde (0.77 g, 2.4 mmol), t-butanol (4.8 ml) and 2-methyl-2-butene (1.71 ml, 16.1 mmol) were mixed, and a solution prepared by mixing sodium chlorite (360 mg, 3.12 mmol), sodium dihydrogenphosphate (374 mg, 3.12 mmol) and water (2.4 ml) was added dropwise. The mixture was stirred at room temperature for 16.5 hours. A 1N aqueous sodium hydroxide solution (5 ml) was added, and t-butanol was evaporated under reduced pressure. Conc. hydrochloric acid was added to make the mixture acidic. Saturated saturated brine (5 ml) was added, and the aqueous layer was extracted 3 times with ethyl acetate (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and the drying agent was filtered off. The filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate to give 1-bromo-4-pentyloxynaphthalene-2-carboxylic acid (619 mg, 76%) as pale-yellow crystals.

Workup

  1. customa solution prepared
  2. additionwas added dropwise
  3. customt-butanol was evaporated under reduced pressure
  4. additionConc. hydrochloric acid was added
  5. additionSaturated saturated brine (5 ml) was added
  6. extractionthe aqueous layer was extracted 3 times with ethyl acetate (10 ml)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eadc08ab68584531b4591fd5a629c30e
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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