HCID 14839276, compound → HCID 14839277, compound

HRID 1646111Notes

Reaction equation

HRID 1646111 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](/[CH:9]=[CH:10]/[C:11](=[O:25])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C)=[O:22])=[CH:16][CH:15]=2)=[CH:4][C:3]=1[CH3:26]>[OH-].[Na+]>[OH:1][C:2]1[C:3]([CH3:26])=[CH:4][C:5](/[CH:9]=[CH:10]/[C:11](=[O:25])[CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:19]=2)=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 1

HCID 14839276HCID 14839276, compound

Product 1

HCID 14839277HCID 14839277, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl (E)-4-[[4-(4-hydroxy-3,5-dimethylphenyl)-2-oxo-3-butenyl]oxy]-benzene acetate (1.73 g) (0.00488 mole) is dissolved in 150 ml 0.1N NaOH and warmed on the steam bath. As soon as a temperature of 70° is reached the reaction mixture is removed from the bath and allowed to cool to 50°, at which point 1N HCl (17 ml) is added slowly. The precipitated solid is filtered off, washed with H2O, and recrystallized from HOAc--H2O to yield yellow crystals, 1.22 g (73%), mp 151°-153.5° C. Anal. for C20H20O5 : Calc. C 70.58, H 5.92; Fd. C 70.48, H 5.72.

Workup

  1. temperaturewarmed on the steam bath
  2. customsoon as a temperature of 70°
  3. customis removed from the bath
  4. temperatureto cool to 50°, at which point 1N HCl (17 ml)
  5. additionis added slowly
  6. filtrationThe precipitated solid is filtered off
  7. washwashed with H2O
  8. customrecrystallized from HOAc--H2O
  9. customto yield yellow crystals, 1.22 g (73%), mp 151°-153.5° C

Sources & evidence

ORD record
ord-8aa8d478e79d4966a8206dfb04e05a49
Source dataset
uspto-grants-1993_01
Patent number
US05177259

Reaction notes

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