Thiophenol → HCID 19855338, compound

HRID 854958Notes

Reaction equation

HRID 854958 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 132969932-(3-Methoxyphenyl)-2-methylpropanal

Product 1

HCID 19855338HCID 19855338, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
212.5 °C

Procedure

To a solution of 2-(3-methoxyphenyl)-2-methylpropanal (20.0 g, 112 mmoles) in 90 mL of N-methylpyrrolidinone was added thiophenol (11.5 mL, 112 mmoles) and anhydrous K2CO3 (1.55 g, 11.2 mmoles). The mixture was stirred at 210-215 ° C. for 3 h. After cooling, the mixture was partitioned between Et2O and 5% aqueous NaOH. The aqueous layer was acidified with dilute HCl and extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered, and evaporated. Chromatography of the residue using 25% EtOAc—hexane as eluent gave the title compound, 10.3 g, as a pale yellow oil.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between Et2O and 5% aqueous NaOH
  3. extractionextracted with DCM
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a19de66661c4486281a79671dab7af78
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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