Water → HCID 18401133, compound

HRID 1183857Notes

Reaction equation

HRID 1183857 reaction equation
[Cl:1]Cl.[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH2:11][C:12]([OH:14])=[O:13].O>C(O)(=O)C>[Cl:1][C:7]1[C:6]([CH3:10])=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[C:4]([CH3:3])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24526ChlorineHCID 198401152-(2,6-Dimethylphenyl)acetic acid

Product 1

HCID 18401133HCID 18401133, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At 10-15° C., 9.22 g [130 mmol] of chlorine gas are slowly introduced into a solution of 16.4 g [100 mmol] of 2,6-dimethylphenylacetic acid in 100 ml of glacial acetic acid. The reaction mixture is then stirred at room temperature for 16 hours and then poured into 500 ml of water. The precipitated solid is filtered off with suction, washed with water and dried. This gives 18.8 g of a white solid which, according to GC(sil.), has the following composition: 86.4% of 3-chloro-2,6-dimethylphenylacetic acid (corresponds to a yield of 81.8% of theory), 8.8% of dichloro-2,6-dimethylphenylacetic acid (isomer 1), 3.8% of dichloro-2,6-dimethylphenylacetic acid (isomer 2).

Workup

  1. filtrationThe precipitated solid is filtered off with suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0ea4bd2a84b24731a149e4e0641eaa14
Source dataset
uspto-grants-2014_03
Patent number
US08664428B2

Reaction notes

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