Water → E 5090

HRID 488133Notes

Reaction equation

HRID 488133 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([OH:21])=[C:6]([O:19][CH3:20])[CH:7]=[C:8]2/[CH:13]=[C:14](\[CH3:18])/[C:15]([OH:17])=[O:16])[CH3:2].[C:22](OC(=O)C)(=[O:24])[CH3:23].O>N1C=CC=CC=1>[C:22]([O:21][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[CH2:1][CH3:2])[C:8](/[CH:13]=[C:14](/[CH3:18])\[C:15]([OH:17])=[O:16])=[CH:7][C:6]=1[O:19][CH3:20])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 6509859(E)-3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-2-methylpropenoic acid

Product 1

HCID 6438616E 5090

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

440 mg of (E)-3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-2-methylpropenoic acid was dissolved in 2.4 ml of pyridine and 0.42 ml of acetic anhydride was added, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and water in this order, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant crystals were washed with hexane to obtain 390 mg of the titled compound as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with dilute hydrochloric acid and water in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe resultant crystals were washed with hexane

Sources & evidence

ORD record
ord-0be3e8f128af415b9ee5b3746272ed5d
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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