Triphenylphosphine → 4-Chloro-3-[2-(2,4-dichloro-phenyl)-ethoxy]-5-methoxy-benzoic Acid Methyl Ester

HRID 967481Notes

Reaction equation

HRID 967481 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([Cl:12])=[C:6](O)[CH:5]=1.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[CH2:23][CH2:24][OH:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([Cl:12])=[C:6]([O:25][CH2:24][CH2:23][C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27340992,4-Dichlorophenethyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 696522944-Chloro-3-hydroxy-5-methoxy-benzoic Acid Methyl Ester

Product 1

HCID 696523074-Chloro-3-[2-(2,4-dichloro-phenyl)-ethoxy]-5-methoxy-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (2.31 mmol) of 4-Chloro-3-hydroxy-5-methoxy-benzoic acid methyl ester was dissolved in 15 ml of anhydrous tetrahydrofuran. To this solution was added 485 mg (2.54 mmol) of 2-(2,4-Dichlorophenyl)-ethanol, 2.3 g (equivalent to 6.92 mmol PPh3) of triphenylphosphine derivatized polystyrene and 1.2 g (6.92 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5).

Workup

  1. filtrationThe polymer was filtered off
  2. washwashed with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5)

Sources & evidence

ORD record
ord-713c7b2f04a44290abeb9f3495660c5d
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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