HCID 18966344, compound → HCID 57138407, compound

HRID 2226174Notes

Reaction equation

HRID 2226174 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([CH3:14])(O)[CH3:12])=[C:6]([SH:8])[CH:7]=1>S(=O)(=O)(O)O>[CH3:12][C:11]1([CH3:14])[CH2:10][C:9]([CH3:16])([CH3:15])[C:5]2[C:6](=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[S:8]1

Participants

3

Reactant 1

HCID 18966344HCID 18966344, compound2×

Product 1

HCID 57138407HCID 57138407, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 10 g (33 mmol) of 5-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol (Compound 35) and 100 ml of 20 percent aqueous sulfuric acid was heated at reflux for 48 hours. The mixture was cooled to room temperature and extracted with 2×50 ml of ether. The ether extracts were combined and washed with 25 ml of saturated sodium bicarbonate solution and 25 ml of saturated NaCl solution and dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash column chromatography (silica: 2% ethyl acetate in hexanes) followed by kugelrohr distillation to give the title compound as a clear oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. extractionextracted with 2×50 ml of ether
  4. washwashed with 25 ml of saturated sodium bicarbonate solution and 25 ml of saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by flash column chromatography (silica: 2% ethyl acetate in hexanes)
  8. distillationfollowed by kugelrohr distillation

Sources & evidence

ORD record
ord-b457ebf5a6bd40d093497c70f499efe0
Source dataset
uspto-grants-1994_09
Patent number
US05346915

Reaction notes

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