p-Toluenesulfonic acid → 4-Methyl-3-pentylfuran-2(5H)-one

HRID 1646161Notes

Reaction equation

HRID 1646161 reaction equation
C(O[C:5]1([CH3:16])[CH2:9][O:8][C:7](=[O:10])[CH:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH3:16][C:5]1[CH2:9][O:8][C:7](=[O:10])[C:6]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 198015774-Acetoxy-4-methyl-3-pentyl-tetrahydrofuran-2-one

Product 1

HCID 159534324-Methyl-3-pentylfuran-2(5H)-oneYield 77.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Acetoxy-4-methyl-3-pentyl-tetrahydrofuran-2-one (125.33 g, 549 mmol) is placed with 2.61 g (13.7 mmol) of p-toluenesulphonic acid and held at 150° C. for 4 hours while stirring. The acetic acid which is cleaved off is distilled off over a Vigreux column. The reaction solution, cooled to room temperature, is diluted with 500 ml of ether and washed in a separating funnel with 2×200 ml of sat. NaCl solution. Drying of the ether phase over MgSO4 and concentration on a rotary evaporator as well as distillation at 100°-103° C./0.12 mbar yields 71.34 g (77.3%) of 4-methyl-3-pentyl-2(5H)furanone.

Workup

  1. distillationis distilled off over a Vigreux column
  2. additionis diluted with 500 ml of ether
  3. washwashed in a separating funnel with 2×200 ml of sat. NaCl solution
  4. dry with materialDrying of the ether phase over MgSO4 and concentration on a rotary evaporator as
  5. distillationwell as distillation at 100°-103° C./0.12 mbar

Sources & evidence

ORD record
ord-2aa26145304d413eb1d2861ccb503d06
Source dataset
uspto-grants-1993_01
Patent number
US05179077

Reaction notes

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