Hydrochloric Acid → N-(2-hydroxyethyl)-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzamide

HRID 264360Notes

Reaction equation

HRID 264360 reaction equation
[CH3:1]/[C:2](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:3]\[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[C:8]([OH:15])[CH:7]=1.S(Cl)(Cl)=O.[OH:26][CH2:27][CH2:28][NH2:29].Cl>CCCCCCCC.N1C=CC=CC=1>[OH:26][CH2:27][CH2:28][NH:29][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([O:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:7][C:8]=1[OH:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 104243134-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid

Product 1

HCID 69130580N-(2-hydroxyethyl)-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzamideYield 22%

Reagents, catalysts & solvents 2

HCID 356OctaneSolventHCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

In 50 ml of n-octane was dissolved 2.00 g (6.9 mmol) of 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid, and 5.0 ml (35 mmol) of thionyl chloride was added to the solution, followed by heating at 90° C. for 5 hours to conduct a reaction. After completion of the reaction, the reaction mixture was cooled, and n-octane was removed by evaporation. The residue was dissolved in n-octane, and a pyridine solution of 0.84 g (13.8 mmol) of 2-hydroxyethylamine was added thereto dropwise at room temperature. After the dropwise addition, the mixture was stirred for 10 minutes, poured into a 12% hydrochloric acid aqueous solution, and extracted with ethyl acetate. The organic layer was washed with water and then with a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The resulting crude product was recrystallized from an ethyl acetate/hexane mixed solvent to obtain 0.50 g (yield: 22%) of N-(2-hydroxyethyl)-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzamide represented by the following structural formula (hereinafter referred to as compound 46) as white crystals. The analytical results are shown below. ##STR67##

Workup

  1. additionwas added to the solution
  2. customa reaction
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. customn-octane was removed by evaporation
  6. dissolutionThe residue was dissolved in n-octane
  7. customdropwise at room temperature
  8. additionAfter the dropwise addition
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with water
  11. dry with materialwith a saturated sodium chloride aqueous solution, dried over sodium sulfate
  12. concentrationconcentrated
  13. customThe resulting crude product was recrystallized from an ethyl acetate/hexane mixed solvent

Sources & evidence

ORD record
ord-95ea6b0de6cb4a58ac0c419a0797285d
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Reaction notes

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