Water → 2-(2,4,5-Trimethylphenyl)acetic acid

HRID 853735Notes

Reaction equation

HRID 853735 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[CH:12][C:8]=1[CH2:9][C:10]#N.[OH2:18]>>[CH3:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[CH:12][C:8]=1[CH2:9][C:10]([OH:2])=[O:18]

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 1447272,4,5-Trimethylphenylacetonitrile

Product 1

HCID 2989242-(2,4,5-Trimethylphenyl)acetic acidYield 90%

Conditions

Temperature
90 °C

Procedure

2118 ml of concentrated sulphuric acid are added dropwise to 2662 ml of water at room temperature and the solution is heated to 90° C. 355 g (2.23 mol) of 2,4,5-trimethyl-benzyl cyanide are metered into the half-concentrated sulphuric acid at this temperature and the mixture is subsequently stirred at 100° C. for 8 hours. After cooling, the reaction mixture is poured into ice-water, while stirring vigorously, and filtered with suction. The solid is washed several times with water and then with petroleum ether and dried. 358 g (90% of theory) of 2,4,5-trimethyl-phenylacetic acid having a melting point of 123-125° C. are obtained.

Workup

  1. temperatureAfter cooling
  2. stirringwhile stirring vigorously
  3. filtrationfiltered with suction
  4. washThe solid is washed several times with water
  5. dry with materialwith petroleum ether and dried

Sources & evidence

ORD record
ord-f4571edf58144c4abc451960a77c64f8
Source dataset
uspto-grants-2007_08
Patent number
US07256158B2

Reaction notes

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