p-Toluenesulfonic acid → HCID 19261766, compound

HRID 1247664Notes

Reaction equation

HRID 1247664 reaction equation
C([O:4][C:5]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CC(C)=O>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:9][C:8]1[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][C:5]([OH:4])=[CH:17][C:16]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:15]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21907769Acetic acid, [[5′-(acetyloxy)[1,1′:3′,1′′-terphenyl]-2′-yl]oxy]-, ethyl ester

Product 1

HCID 19261766HCID 19261766, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 4-acetoxy-2,6-diphenylphenoxyacetate (7.2 g, 18.5 mmol) was dissolved in wet toluene (400 ml) and a catalyst (25 g SiO2 treated with a solution of 2 g 4-toluenesulfonic acid in 10 ml acetone and evaporated in vacuo) was added. The mixture was stirred and heated at 100° C. for 6 h, cooled and filtered through a column of silica gel (50 g). Elution with benzene afforded 3.6 g (56%) of (2,6-diphenyl-4-hydroxy-phenoxy)-acetic acid ethyl ester as white crystals, which were recrystallized from benzene/petroleum ether. M.p. 91–93° C.

Workup

  1. customevaporated in vacuo)
  2. additionwas added
  3. temperaturecooled
  4. filtrationfiltered through a column of silica gel (50 g)
  5. washElution with benzene

Sources & evidence

ORD record
ord-6cb47bade2f14693ab5a19b457648ca8
Source dataset
uspto-grants-2006_10
Patent number
US07129268B2

Reaction notes

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