Hydrochloric Acid → 2-acetoxy-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}benzoic acid

HRID 264359Notes

Reaction equation

HRID 264359 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:11])=[C:8]([OH:15])[CH:7]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].Cl>N1C=CC=CC=1>[C:22]([O:15][C:8]1[CH:7]=[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:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 104243134-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid

Product 1

HCID 691303622-acetoxy-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}benzoic acidYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 10 ml of a pyridine solution containing 0.82 g (2.82 mmol) of 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid was added 0.72 g (7.1 mmol) of acetic anhydride, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into a 2% hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed successively with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The resulting crude product was recrystallized from an ethyl ether/hexane mixed solvent to obtain 0.45 g (yield: 48%) of 2-acetoxy-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}benzoic acid represented by the following structural formula (hereinafter referred to as compound 45) as white crystals. The analytical results are shown below. ##STR66##

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water
  3. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product was recrystallized from an ethyl ether/hexane mixed solvent

Sources & evidence

ORD record
ord-169ba451713944ffb01cacfa03df35c5
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Reaction notes

Loading…