Water → Furan, 2-methyl-4-phenyl-

HRID 414644Notes

Reaction equation

HRID 414644 reaction equation
[O:1]1[CH2:6][C:2]1([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]#[CH:5].O>C(O)C>[CH3:5][C:4]1[O:1][CH:6]=[C:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 14028120HCID 14028120, compound

Product 1

HCID 11008190Furan, 2-methyl-4-phenyl-Yield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 0.5 g HgSO4 in 30 mL of 2N HgSO4 was added 4.74 g (30 mmol) of 4,5-epoxy-4-phenyl-1-pentyne in 30 mL of absolute ethanol over a 5 minute period. The reaction mixture was refluxed for 0.25 hour and cooled to 23° C. After addition to 150 mL of H2O the mixture was extracted with hexanes three times. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Sublimination (90° C. at 15 mmHg) of the solid gave 3.6 g (76%) of 2-methyl-4-phenylfuran as a solid (m.p. 89°-91° C.) which was homogeneous by spectroscopic considerations; IR (KBr) 1599, 1545, 1440, 742 cm-1 ; 1HNMR (300 MHz, CDCl3) δ 7.62 (s, 1H), 7.50 (d, 2H, J=9.0 Hz), 7.38 (t, 2H, J=9.0 Hz), 7.28 (t, 1H, J=9.0 Hz), 6.33 (s, 1H), 2.35 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 0.25 hour
  2. extractionwas extracted with hexanes three times
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08ce3cb7ba5e42cba27c14e66ed8fa5e
Source dataset
uspto-grants-1988_12
Patent number
US04792614

Reaction notes

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