Water → HCID 69130364, compound

HRID 264361

Reaction equation

HRID 264361 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[CH2:12](Br)/[CH:13]=[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:15].O>CN(C=O)C>[CH3:15]/[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:13]\[CH2:12][NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 46494-Aminosalicylic AcidHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Product 1

HCID 69130364HCID 69130364, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of DMF was dissolved 2.12 g (13.8 mmol) of 4-amino-2-hydroxybenzoic acid, and 3.0 g (13.8 mmol) of geranyl bromide was added thereto. After the mixture was stirred at room temperature for 4 hours, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated. The resulting crude product was purified by column chromatography and recrystallized from ethyl acetate/hexane to obtain 0.30 g (yield: 7.6%) of N-{(2E)-3,7-dimethylocta-2,6-dienyl}-4-amino-2-hydroxybenzoic acid represented by the following structural formula (hereinafter referred to as compound 47) as white crystals. The analytical results are shown below. ##STR68##

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by column chromatography
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5316f008abab4fd7b2c48ac561965c04
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Linked notes

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