Nitromethane → HCID 20373875, compound

HRID 1834685Notes

Reaction equation

HRID 1834685 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])[CH:4]([CH3:18])[CH:3]1[CH2:19][CH3:20].[Cl:21]Cl.[N+](C)([O-])=O>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])[CH:4]([CH3:18])[C:3]1([CH2:19][CH3:20])[Cl:21]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 24526ChlorineHCID 12395536HCID 12395536, compound

Product 1

HCID 20373875HCID 20373875, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a suspension of (1-oxo-2-ethyl-3-methyl-6,7-dichloro-5-indanyloxy)acetic acid (3.5 g., 0.011 mole) in glacial acetic acid (75 ml.) and concentrated hydrochloric acid (2 drops) is added, with stirring, a solution of glacial acetic acid (50 ml.) and chlorine (0.9 g., 0.0127 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. The yield of product is 3.6 g. (93% yield) of (1-oxo-2-ethyl-3-methyl-2,6,7-trichloro-5-indanyloxy)acetic acid which, after recrystallization from nitromethane, melts at 208.5°-210.5° 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

Sources & evidence

ORD record
ord-5f2f5b219fbb49a1a9c902d0b32cfa0e
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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