p-Toluenesulfonic acid → Carvacrol

HRID 1584066Notes

Reaction equation

HRID 1584066 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][C:13]1[C:18](=[O:19])[CH2:17][CH:16]([C:20]([CH3:22])=[CH2:21])[CH2:15][CH:14]=1>ClC1C=CC=CC=1.O1CCOCC1>[CH:17]1[C:16]([CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=[C:13]([CH3:12])[C:18]=1[OH:19]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 7439Carvone, (+-)-

Product 1

HCID 10364CarvacrolYield 85%

Reagents, catalysts & solvents 1

HCID 70620864HCID 70620864, compoundSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of p-toluenesulfonic acid (1.4 g) and carvone (11.3 g) in chlorobenzene/1,4-dioxane (4:1 by volume; 75 mL) was heated at 180° C. for 35 min, then rapidly cooled using the cold-finger, and extracted with 10% NaOH solution (3×100 mL). The combined aqueous extract was washed with CH2Cl2 (2×100 mL), neutralized by dropwise addition of conc H2SO4, and extracted with CH2Cl2 (3×100 mL). The organic extract was washed with sat NaHCO3 (100 mL), dried with MgSO4, and concentrated in vacuo to give carvacrol (9.6 g; 85%).

Workup

  1. temperaturerapidly cooled
  2. extractionextracted with 10% NaOH solution (3×100 mL)
  3. extractionThe combined aqueous extract
  4. washwas washed with CH2Cl2 (2×100 mL)
  5. additionneutralized by dropwise addition of conc H2SO4
  6. extractionextracted with CH2Cl2 (3×100 mL)
  7. extractionThe organic extract
  8. washwas washed with sat NaHCO3 (100 mL)
  9. dry with materialdried with MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e8941bc0fe042ceb133f496e90ca512
Source dataset
uspto-grants-1999_08
Patent number
US05932075

Reaction notes

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