O-Cresol → HCID 4739205, compound

HRID 1781149Notes

Reaction equation

HRID 1781149 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.CCCCCC.C(OCC)(=O)C>CS(C)=O>[CH3:8][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[O:7][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 335O-CresolHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 4739205HCID 4739205, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

A solution of o-cresol (5.4 g, 50.7 mmol) in DMSO (10 mL) was added dropwise to a stirred mixture of 60% oil dispersion sodium hydride (2.02 g, 50.5 mmol) in DMSO (20 mL). After stirring for 1 hour at ambient temperature, a solution of p-fluorobenzaldehyde (5.36 mL, 50 mmol) in DMSO (10 mL) was added dropwise. After the addition was complete, the reaction mixture was gradually heated to 140-160° C. and maintained at that temperature for 1 hour. The reaction mixture was poured into ice-water and extracted with ether. The combined organic extracts were washed successively with ice-cold dilute aqueous sodium hydroxide solution, dilute aqueous hydrochloric acid solution, water and saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated to give a brown liquid. Chromatography on silica gel eluting with 95:5 hexane-ethyl acetate afforded 6.1 g (51%).of the title compound. 1H NMR (CDCl3, 300MHz) δ 2.19 (s, 3H), 6.98 (m, 3H), 7.2 (m, 3H), 7.82 (m, 2H), 9.9 (s, 1H). MS (DCl/NH3) m/e 213 (M+H)+.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was gradually heated to 140-160° C.
  3. temperaturemaintained at that temperature for 1 hour
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed successively with ice-cold dilute aqueous sodium hydroxide solution, dilute aqueous hydrochloric acid solution, water and saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give a brown liquid

Sources & evidence

ORD record
ord-16b07fe1a84947d183d74da1474fda1b
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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