Hydrochloric Acid → HCID 10447045, compound

HRID 863608Notes

Reaction equation

HRID 863608 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]([OH:14])=[O:13])[C:6]=2[C:15]=1[CH3:16].[C:19](OC(=O)C)(=[O:21])[CH3:20].O.Cl>N1C=CC=CC=1>[C:19]([O:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]([OH:14])=[O:13])[C:6]=2[C:15]=1[CH3:16])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 10131175HCID 10131175, compound

Product 1

HCID 10447045HCID 10447045, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 25.03 g (0.1M) of 2,3-dihydro-5-hydroxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid (described in Example 1) in 200 ml of pyridine is added 100 ml of acetic anhydride and the mixture is stirred at room temperature for 24 hours. Water and ice is added and the mixture is stirred at about 30° C. for 30 minutes. More ice and 450 ml of 6N hydrochloric acid is added and the resulting solid is collected, washed with water, and taken up in ethyl acetate. The solution is washed with 2N hydrochloric acid and water and is dried over anhydrous sodium sulfate. The residue obtained after filtration and evaporation of solvent is recrystallized from ethyl acetate to give 23.6 g (81%) of the title compound as racemate, m.p. 187°-8° C. Elemental analysis, UV, and 1H-NMR spectra confirm the structure.

Workup

  1. stirringthe mixture is stirred at about 30° C. for 30 minutes
  2. customthe resulting solid is collected
  3. washwashed with water
  4. washThe solution is washed with 2N hydrochloric acid and water
  5. dry with materialis dried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. filtrationafter filtration and evaporation of solvent
  8. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-228be8fb6ce14b629e4cc5ff88e2521b
Source dataset
uspto-grants-1998_02
Patent number
US05721233

Reaction notes

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