HCID 10355440, compound → HCID 10131175, compound

HRID 863605Notes

Reaction equation

HRID 863605 reaction equation
[OH:1][C:2]1[C:3]([CH3:19])=[C:4]([CH3:18])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]([O:14]C)=[O:13])[C:6]=2[C:16]=1[CH3:17]>CO.[OH-].[Na+]>[OH:1][C:2]1[C:3]([CH3:19])=[C:4]([CH3:18])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]([OH:14])=[O:13])[C:6]=2[C:16]=1[CH3:17]

Participants

4

Reactant 1

HCID 10355440HCID 10355440, compound

Product 1

HCID 10131175HCID 10131175, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Refluxing 22.36 g of the above material (see Step C) in 100 ml of methanol and 100 ml of 2N sodium hydroxide for 24 hours is followed by acidification with 120 ml of 2N hydrochloric acid, evaporation of methanol, and extraction with ethyl acetate (twice). The extract is washed with water and acidic product is extracted into a sodium bicarbonate solution, which upon acidification is reextracted with ethyl acetate. The extract is dried over sodium sulfate, filtered and evaporated. The resulting solid is recrystallized from ethyl acetate/heptane to give 16.40 g (77%) of 2,3-dihydro-5-hydroxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid, m.p. 161°-164° C. Elemental analysis, IR, UV, and 1H-NMR spectra confirm the structure.

Workup

  1. customis followed by acidification with 120 ml of 2N hydrochloric acid, evaporation of methanol, and extraction with ethyl acetate (twice)
  2. washThe extract is washed with water and acidic product
  3. extractionis extracted into a sodium bicarbonate solution, which upon acidification
  4. dry with materialThe extract is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting solid is recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-a20e3415e02d4ae585d9fd0a4112b1f7
Source dataset
uspto-grants-1998_02
Patent number
US05721233

Reaction notes

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