p-Toluenesulfonic acid → Pentyl hydroxy(phenyl)acetate

HRID 641128

Reaction equation

HRID 641128 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH2:14](O)[CH2:15][CH2:16]CC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCCCC)(=O)C>[C:1]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 62761-PentanolHCID 13050Ethyl mandelate

Product 1

HCID 347424Pentyl hydroxy(phenyl)acetate

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

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 7.94 grams of ethyl mandelate, 40 mL of 1-pentanol, and 0.75 gram of p-toluenesulfonic acid. The reaction was stirred at 120°-132° C. for 4.0 hours with a nitrogen sweep. The reaction mixture was taken up in butyl acetate, extracted with dilute aqueous sodium hydroxide, washed three times with water, dried over magnesium sulfate, and filtered. Solvent was removed by rotary evaporation to yield 8.3 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 hydroxide
  3. washwashed three times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customSolvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-506dd38d84574e3fb2043200e9fd0cae
Source dataset
uspto-grants-2010_04
Patent number
US07696136B2

Linked notes

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