Sulfur → 4-tert-Butyl-1-benzofuran-5-ol

HRID 1089621Notes

Reaction equation

HRID 1089621 reaction equation
C([C:5]1[O:6][C:7]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C:8]=2[CH:9]=1)(C)(C)C.[S]>>[C:8]([C:10]1[C:8]2[CH:9]=[CH:5][O:6][C:7]=2[CH:13]=[CH:12][C:11]=1[OH:14])([CH3:10])([CH3:9])[CH3:7]

Participants

3

Reactant 2

HCID 5362487SulfurHCID 54301121Tert butyl-4,5,6,7 tetrahydro-5-benzofuranone

Product 1

HCID 141432464-tert-Butyl-1-benzofuran-5-ol

Conditions

Temperature
225 °C

Procedure

A mixture of 4 tert butyl-4,5,6,7 tetrahydro-5-benzofuranone (1.00 g, 5.2 mmol) and sulfur (0.167 g, 1 equivalent) in a sealable tube is flushed with nitrogen, sealed and heated to 225° C. for 30 minutes. An additional portion of sulfur (0.030 g) is then added and the mixture heated an additional 15 minutes. After cooling the total reaction mixture is taken up in a small portion of methylene chloride and applied directly to a flash silica gel column. Elution with 5% ethyl acetate in hexane gives 4-tert-butyl5-benzofuranol.

Workup

  1. customis flushed with nitrogen
  2. customsealed
  3. additionAn additional portion of sulfur (0.030 g) is then added
  4. temperaturethe mixture heated an additional 15 minutes
  5. temperatureAfter cooling the total reaction mixture
  6. washElution with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-460ae84ccb5642d0a2d60187e0daf816
Source dataset
uspto-grants-1990_10
Patent number
US04966907

Reaction notes

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