2,4-Dichlorophenol → HCID 22930531, compound

HRID 2247425Notes

Reaction equation

HRID 2247425 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1O.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:30][O:16][C:15](=[O:17])[C:14]1[CH:18]=[CH:19][CH:20]=[C:12]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([CH2:3][CH2:2][O:1][C:25]3[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][C:26]=3[Cl:28])[CH:5]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 84492,4-DichlorophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68633879HCID 68633879, compound

Product 1

HCID 22930531HCID 22930531, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

53 mg of 3-[3-(2-hydroxyethyl)-4-methoxyphenyl]benzoic acid, 45 mg of 2,4-dichlorophenol and 73 mg of triphenyl phosphine were dissolved in 2 ml of THF, and 73 ml of diisopropyl azodicarboxylate was added thereto. The mixture was stirred overnight at room temperature, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give 84 mg of methyl-3-{3-[2-(2,4-dichlorophenoxy)ethyl]-4-methoxyphenyl}benzoate. This product was dissolved in 2 ml of of ethanol and 0.5 ml of 5N sodium hydroxide and then heated. The reaction mixture was neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The solvent was evaporated to give 42 mg of the title compound.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-736d6f4860a04f1ea78affa38d314012
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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