4-Methoxyphenylacetic Acid → 1-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanone

HRID 1958677Notes

Reaction equation

HRID 1958677 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][CH:14]=1.[Cl:23][C:24]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:25]=1C(OC)=O>C1COCC1>[Cl:23][C:24]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:25]=1[C:20](=[O:22])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 76904-Methoxyphenylacetic AcidHCID 37055Methyl 2,4-dichlorobenzoateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 610554751-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanoneYield 45.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

367 ml of NaHMDS (2M in THF) are added to 250 ml of THF and the mixture is cooled to −70° C. 54 g of (4-methoxyphenyl)acetic acid are then added; the mixture is left stirring for 2 hours and then 49 g of methyl 2,4-dichlorobenzoate are added. The reaction mixture is allowed to return to 10° C. and poured onto 2 liters of ice-cold HCl (2N), and the product is extracted with ether. After drying with a saturated sodium bicarbonate solution and then a saturated NaCl solution, drying the organic phase and evaporating, the product crystallizes from heptane; 32 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. customto return to 10° C.
  3. extractionthe product is extracted with ether
  4. dry with materialAfter drying with a saturated sodium bicarbonate solution
  5. dry with materiala saturated NaCl solution, drying the organic phase
  6. customevaporating
  7. customthe product crystallizes from heptane

Sources & evidence

ORD record
ord-7a2faca018854262b669ee1c388f3440
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

Loading…