p-Toluenesulfonic acid → HCID 22004691, compound

HRID 324666Notes

Reaction equation

HRID 324666 reaction equation
O[C:2]1([C:17]([OH:19])=[O:18])[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH2:6][CH2:5][C:4](=[O:16])[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:7]1[C:2]([C:17]([OH:19])=[O:18])=[CH:3][C:4](=[O:16])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22004694HCID 22004694, compound

Product 1

HCID 22004691HCID 22004691, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

396.7 g (1.5 mol) of 1-hydroxy-6-(2-methoxyphenyl)-3-oxocyclohexane-1-carboxylic acid were heated at reflux for two hours in 13.3 dm3 of toluene in the presence of 39.7 g of para-toluenesulphonic acid. The reaction mixture was subsequently concentrated under reduced pressure and the precipitate formed was filtered off, washed with isopropyl ether and then dried at 50° C. 288 g (78%) of (RS)-6-(2-methoxyphenyl)-3-oxocyclohexene-1-carboxylic acid were thus obtained in the form of a brown solid, the characteristics of which were as follows:

Workup

  1. concentrationThe reaction mixture was subsequently concentrated under reduced pressure
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with isopropyl ether
  5. customdried at 50° C

Sources & evidence

ORD record
ord-eff98ace2b6a4d89b847695643161906
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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