Triphenylphosphine → Methyl 4-[(2-phenoxyphenyl)methoxy]benzeneacetate

HRID 384122Notes

Reaction equation

HRID 384122 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:16][O:17][C:18](=[O:27])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:15][CH2:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 36601112-Phenoxybenzyl alcohol

Product 1

HCID 131730197Methyl 4-[(2-phenoxyphenyl)methoxy]benzeneacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-phenoxyphenyl)methanol (1.43 g) in tetrahydrofuran (25 ml), 1.19 g of methyl(4-hydroxyphenyl)acetate, 2.82 g of triphenylphosphine, and 4.86 ml of diethyl azodicarboxylate (45% toluene solution) were added, and the reaction solution was stirred at room temperature for 30 minutes. The reaction solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (5:95-30:70)) to afford the title compound as a colorless oil.

Workup

  1. distillationThe reaction solvent was distilled off under reduced pressure
  2. customthe residue obtained
  3. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (5:95-30:70))

Sources & evidence

ORD record
ord-4047015b89544303a7efc9d35252450d
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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