p-Toluenesulfonic acid → 2,3,4,5-tetramethylfuran

HRID 723657Notes

Reaction equation

HRID 723657 reaction equation
[CH3:1][CH:2]([CH:6]([CH3:10])[C:7](=[O:9])[CH3:8])[C:3](=O)[CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:4][C:3]1[O:9][C:7]([CH3:8])=[C:6]([CH3:10])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 328513,4-Dimethylhexane-2,5-dione

Product 1

HCID 1391982,3,4,5-tetramethylfuranYield 19.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3,4-dimethylhexane-2,5-dione (3.00 g, 21.1 mmol) and p-toluenesulfonic acid (401 mg, 2.11 mmol) in benzene (30 mL) was heated to reflux in a Dean-Stark trap overnight. The reaction mixture was distilled at atmospheric pressure to remove the excess benzene. The remaining mixture was transferred to a smaller flask and distilled at atmospheric pressure. The fraction that came over between 80–100° C. was collected to give 509 mg (19%) of compound 219A as a light yellow oil.

Workup

  1. temperatureto reflux in a Dean-Stark trap overnight
  2. distillationThe reaction mixture was distilled at atmospheric pressure
  3. customto remove the excess benzene
  4. customThe remaining mixture was transferred to a smaller flask
  5. distillationdistilled at atmospheric pressure
  6. customcame over between 80–100° C.
  7. customwas collected

Sources & evidence

ORD record
ord-62e8ac59efc64eb3a20d463bd21499db
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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