Triphenylphosphine → 3-[2-(2,4-Dichlorophenyl)-ethoxy]-4-methoxy-benzoic Acid Methyl Ester

HRID 967438Notes

Reaction equation

HRID 967438 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([OH:31])[CH:24]=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][CH2:54]O>C1COCC1>[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:54][CH2:53][C:47]2[CH:48]=[CH:49][C:50]([Cl:52])=[CH:51][C:46]=2[Cl:45])[CH:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27340992,4-Dichlorophenethyl alcoholHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 693063413-[2-(2,4-Dichlorophenyl)-ethoxy]-4-methoxy-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

20 g of triphenylphosphine and 10 g of 3-Hydroxy-4-methoxy-benzoic acid methyl ester were dissolved in 200 ml of anhydrous THF. The solution was cooled to 0° C. to 10° C. and a solution of 11.4 ml DEAD in 30 ml anhydrous THF was added dropwise over 20 min. The reaction was warmed to RT and stirred for 45 min. A solution of 11.3 ml 2-(2,4-Dichlorophenyl)-ethanol in 10 ml anhydrous THF was added with cooling. The reaction was stirred at RT for 16 h, and then the solvents were removed under reduced pressure. The residue was treated with n-heptane:ethyl acetate/1:1. The filtrate was dried under reduced pressure. The product was purified by silica gel chromatography, eluting with n-heptane:ethyl acetate/4:1, then n-heptane:ethyl acetate/3:1.

Workup

  1. temperatureThe solution was cooled to 0° C. to 10° C.
  2. temperaturewith cooling
  3. stirringThe reaction was stirred at RT for 16 h
  4. customthe solvents were removed under reduced pressure
  5. additionThe residue was treated with n-heptane
  6. customThe filtrate was dried under reduced pressure
  7. customThe product was purified by silica gel chromatography
  8. washeluting with n-heptane

Sources & evidence

ORD record
ord-c8414d11bf51474ea011ae3fe6556c27
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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