p-Toluenesulfonic acid → HCID 54534149, compound

HRID 265347Notes

Reaction equation

HRID 265347 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:12][CH:13]1[C:20](OC)([O:21]C)[CH2:19][CH2:18][C:15]2([O:17][CH2:16]2)[C:14]1([OH:29])[C:25]([CH3:28])=[CH:26][CH3:27]>CC(C)=O.O>[Br:12][CH:13]1[C:20](=[O:21])[CH2:19][CH2:18][C:15]2([O:17][CH2:16]2)[C:14]1([OH:29])[C:25]([CH3:28])=[CH:26][CH3:27]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57209017HCID 57209017, compound

Product 1

HCID 54534149HCID 54534149, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

1.9 g (9.96 mmol) of para-toluenesulphonic acid are added at room temperature to a solution of 3.2 g (9.96 mmol) of the compound obtained in Step B in 120 ml of an acetone/water mixture (3:2). When the reaction, followed by thin-layer chromatrography, is complete, the acetone is evaporated off. The aqueous phase remaining is then extracted with ethyl acetate (200 ml). After conventional treatment of the organic phase, 2.23 g (8.1 mmol) of the expected product are obtained.

Workup

  1. customWhen the reaction
  2. customthe acetone is evaporated off
  3. extractionThe aqueous phase remaining is then extracted with ethyl acetate (200 ml)

Sources & evidence

ORD record
ord-cc72602fce3f4cb2afa94d36a0ef7459
Source dataset
uspto-grants-1997_07
Patent number
US05648382

Reaction notes

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