p-Toluenesulfonic acid monohydrate → HCID 56638504, compound

HRID 1388215Notes

Reaction equation

HRID 1388215 reaction equation
[CH2:1]([O:5][C:6](=[O:16])[CH:7](O)[C:8]1[C:9](=O)[CH2:10][CH:11]([CH3:13])[CH:12]=1)[CH2:2][CH2:3][CH3:4].O.C1(C)C=CC(S(O)(=O)=[O:25])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6](=[O:16])[CH:7]=[C:8]1[CH2:12][CH:11]([CH3:13])[C:10](=[O:25])[CH2:9]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 54368153HCID 54368153, compound

Product 1

HCID 56638504HCID 56638504, compoundYield 1,072.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
15 °C

Procedure

Into a 5-L, 3-necked, round-bottomed flask equipped with a condenser, thermometer and nitrogen inlet were added 154.8 g (0.68 M) alpha-hydroxy-4-methyl-3-oxo-cyclopentene acetic acid butyl ester (as prepared by Example 4), 2.3 L of toluene, and 12.9 g (0.068 M) of p-toluenesulfonic acid monohydrate. The resulting reaction mixture was stirred at 75°-78° C. for 61/2 hours under nitrogen. When the reaction was complete, the mixture was cooled to 15° C., poured into a separatory funnel, washed with three 1-L portions of a total of 3 L of water, dried (MgSO4) and evaporated to give 153 g of the homogeneous 4-methyl-3-oxo-cyclopentylidene acetic acid butyl ester bp 82°-84° C./0.05 mm Hg, as a red oil for use in Example 8.

Workup

  1. customThe resulting reaction mixture
  2. additionpoured into a separatory funnel
  3. washwashed with three 1-L portions of a total of 3 L of water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5ab69cf7e8054b18a42ea073aff12640
Source dataset
uspto-grants-1984_02
Patent number
US04430507

Reaction notes

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