Butyl Chloride → HCID 20373873, compound

HRID 1834683Notes

Reaction equation

HRID 1834683 reaction equation
ClCl.[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[C:10]([Cl:14])[C:11]=2[Cl:13])[CH2:6][CH:5]1[CH2:20][CH:21]([CH3:23])[CH3:22].C([Cl:28])CCC>C(O)(=O)C.Cl>[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[C:10]([Cl:14])[C:11]=2[Cl:13])[CH2:6][C:5]1([CH2:20][CH:21]([CH3:23])[CH3:22])[Cl:28]

Participants

6

Reactant 3

HCID 8005Butyl ChlorideHCID 24526ChlorineHCID 20373882HCID 20373882, compound

Product 1

HCID 20373873HCID 20373873, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of glacial acetic acid (50 ml.) and chlorine (0.40 g., 0.00565 mole) is added with stirred over a 10-minute period to a suspension of (1-oxo-2-isobutyl-6,7-dichloro-5-indanyloxy)acetic acid (1.6 g., 0.00485 mole) in glacial acetic acid (50 ml.) and concentrated hydrochloric acid (1 drop). 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 (200 ml.). The white solid thatseparates is collected by filtration, washed in water and dried to afford 1.0 g. (56% yield) of (1-oxo-2-isobutyl-2,6,7-trichloro-5-indanyloxy)acetic acid which after recrystallization from n-butyl chloride melts at 166° C.

Workup

  1. additionDuring the addition the reaction vessel
  2. temperatureis heated on a steam bath
  3. additionAfter the addition
  4. temperaturewithout heating for 30 minutes
  5. filtrationThe white solid thatseparates is collected by filtration
  6. washwashed in water
  7. customdried
  8. customto afford 1.0 g

Sources & evidence

ORD record
ord-2df72747f9894510af227ef897db38be
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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