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

HRID 585468Notes

Reaction equation

HRID 585468 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-trimethylphenylacetic 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-6512ae7d2b264c009b226092828e3ed0
Source dataset
uspto-grants-2005_08
Patent number
US06933261B2

Reaction notes

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