p-Toluenesulfonic acid → HCID 67071775, compound

HRID 641129Notes

Reaction equation

HRID 641129 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.C(O)[CH2:17][CH2:18][CH2:19][CH3:20].[C:22]1(C)[CH:27]=CC(S(O)(=O)=O)=[CH:24][CH:23]=1>>[CH2:10]([O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([OH:14])[CH:13]=[C:4]([C:3]([O:2][CH2:1][CH2:20][CH2:19][CH2:18][CH3:17])=[O:15])[CH:5]=1)[CH2:27][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 62761-PentanolHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 67071775HCID 67071775, compound

Conditions

Temperature
129 °C

Procedure

A 100 mL three-neck flask, equipped with a magnetic stir bar, a Claisen adapter with a thermocouple and a subsurface nitrogen inlet, and a short path condenser, was charged with 5.31 grams of dimethyl-5-hydroxyisophthalate, 44 mL of 1-pentanol, and 0.53 gram of p-toluenesulfonic acid. The reaction was stirred at 129° C. for 6.3 hours with a nitrogen sweep. The reaction mixture was taken up in xylenes, extracted with dilute aqueous sodium bicarbonate, washed twice with water, dried over magnesium sulfate, and filtered. Solvent was removed by rotary evaporation to yield 7.3 grams of a straw-colored liquid.

Workup

  1. customA 100 mL three-neck flask, equipped with a magnetic stir bar
  2. extractionextracted with dilute aqueous sodium bicarbonate
  3. washwashed twice with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customSolvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-4da2dad4fe8240faa1918acad976fbd5
Source dataset
uspto-grants-2010_04
Patent number
US07696136B2

Reaction notes

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