Sulfuric Acid → HCID 19825785, compound

HRID 2249210Notes

Reaction equation

HRID 2249210 reaction equation
S(=O)(=O)(O)O.O[C:7]([CH:10]1[CH2:14][C:13]2[CH:15]=[C:16]([OH:21])[C:17]([O:19][CH3:20])=[CH:18][C:12]=2[O:11]1)([CH3:9])[CH3:8]>>[OH:21][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:12]2[O:11][C:10]([CH:7]([CH3:9])[CH3:8])=[CH:14][C:13]=2[CH:15]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 19825784HCID 19825784, compound

Product 1

HCID 19825785HCID 19825785, compoundYield 43.5%

Procedure

To a solution of conc. sulfuric acid (1 ml) was added 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-6-methoxy-5-benzofuranol (50 mg) in several portions during a period of few minutes. The mixture was stirred for 10 minutes at ambient temperature and poured into ice water. The separated oil was extracted with methylene chloride. The organic layer was washed with water, dried, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (n-hexane/methylene chloride =1/1) to yield 5-hydroxy-6-methoxy-2-(1-methylethyl)benzofuran (20 mg) as crystals.

Workup

  1. extractionThe separated oil was extracted with methylene chloride
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (n-hexane/methylene chloride =1/1)

Sources & evidence

ORD record
ord-41ac6b771af64590ad03b6e1d14da17b
Source dataset
uspto-grants-1991_08
Patent number
US05043354

Reaction notes

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