Chlorine → (1-Oxo-2-ethyl-2,6,7-trichloro-5-indanyloxy)acetic acid

HRID 1834686Notes

Reaction equation

HRID 1834686 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][CH:3]1[CH2:18][CH3:19].[Cl:20]Cl>C(O)(=O)C.Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH2:18][CH3:19])[Cl:20]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 33794Acetic acid, 6,7-dichloro-2-ethyl-1-oxo-5-indanyloxy-

Product 1

HCID 20373859(1-Oxo-2-ethyl-2,6,7-trichloro-5-indanyloxy)acetic acidYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a suspension of (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid (6.06 g., 0.02 mole) in glacial acetic acid (100 ml.) and concentrated hydrochloric acid (2 drops) is added, with stirring, a solution of glacial acetic acid (50 ml.) and chlorine (1.56 g., 0.22 mole) over a period of 10 minutes. During the addition the reaction vessel is heated on a steam bath. After the addition is complete, the mixture is stirred without heating for 30 minutes and then poured into ice water (600 ml.). The white solid that separates is collected by filtration, washed with water and dried to afford 6.6 g. (98% yield) of (1-oxo-2-ethyl-2,6,7-trichloro-5-indanyloxy)acetic acid, m.p. 185°-187° C. After recrystallization from acetic acid (25 ml.) the yield of (1-oxo-2-ethyl-2,6,7-trichloro-5-indanyloxy)acetic acid is 5.7 g., m.p. 186°-188° C.

Workup

  1. additionis added
  2. additionDuring the addition the reaction vessel
  3. temperatureis heated on a steam bath
  4. additionAfter the addition
  5. stirringthe mixture is stirred
  6. temperaturewithout heating for 30 minutes
  7. filtrationThe white solid that separates is collected by filtration
  8. washwashed with water
  9. customdried
  10. customto afford 6.6 g

Sources & evidence

ORD record
ord-31c717f273ad4f9a96103b65ee79688b
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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