p-Toluenesulfonic acid monohydrate → HCID 69078742, compound

HRID 458743Notes

Reaction equation

HRID 458743 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.O.[C:14]1([CH3:24])[CH:19]=CC(S(O)(=O)=O)=C[CH:15]=1.[CH3:25]CCCCC.C1(C)C=CC=CC=1>C(=O)C(C)(C)C.C(OCC)(=O)C>[C:14]([C@H:24]1[O:10][C:9](=[O:11])[C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[O:12]1)([CH3:25])([CH3:19])[CH3:15]

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 785085(2R)-(4-Chlorophenyl)(hydroxy)acetic acidHCID 21889329Toluene hexane

Product 1

HCID 69078742HCID 69078742, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 12417PivalaldehydeSolvent

Procedure

To a solution of 16 g of (2R)-2-(4-chlorophenyl)-2-hydroxyacetic acid (cf. JP-Hei 6 (1994)-165695A) in 440 ml of hexane/toluene (10:1), 23 ml of pivalaldehyde and 326 mg of p-toluenesulfonic acid monohydrate were added by the order stated, followed by 12 hours' heating under reflux while removing the generated water with Dean-Stark trap. The reaction liquid was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 14 g of the title compound was obtained.

Workup

  1. temperature' heating
  2. temperatureunder reflux
  3. customwhile removing the generated water with Dean-Stark trap
  4. customThe reaction liquid
  5. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-9800b99f95934e08a978c70ac09e49f6
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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