p-Toluenesulfonic acid → HCID 53897219, compound

HRID 2256944Notes

Reaction equation

HRID 2256944 reaction equation
[CH:1]1([C:4](=[O:25])[CH:5]([C:13](=[O:24])[C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])C(OC(C)(C)C)=O)[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:25])[CH2:5][C:13]([C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])=[O:24])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53651851HCID 53651851, compound

Product 1

HCID 53897219HCID 53897219, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of t-butyl 3-cyclopropyl-2-(2-methoxy4-methylsulphenylbenzoyl)-3-oxopropionate (35.1 g) and 4-toluenesulphonic acid (1.2 g) in toluene was stirred and heated at reflux for 8 hours. After cooling, it was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 3-cyclopropyl-1-(2-methoxy-4-methylsulphenylphenyl)-propan-1,3-dione (25.8 g) as a red solid, NMR (CDCl3); 0.7-1.2 (m,4H), 1.4-2.0 (m, 1H), 2.4(s,3H), 3.75 (s,3H), 6.4(s, 1H), 6.6(s, 1H), 6.65 (d, 1H) and 7.65 (d, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. temperatureAfter cooling
  4. washit was washed with water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ac00c23fee8e4157b1e48a5f845b0a2d
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

Loading…