Chloroform → HCID 12761138, compound

HRID 597019Notes

Reaction equation

HRID 597019 reaction equation
[CH:1]1([C:6]2([CH3:19])[CH2:14][C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=3)[CH:7]2[OH:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:20].[Na+].C(Cl)(Cl)Cl>CC(C)=O>[CH3:1][C:6]([O:15][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]([Cl:17])[C:10]=1[Cl:16])[C:7](=[O:18])[C:6]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)([CH3:19])[CH2:14]2)([CH3:14])[C:7]([OH:18])=[O:20]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 21449489HCID 21449489, compound

Product 1

HCID 12761138HCID 12761138, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a refluxing solution of 2-cyclopentyl-2-methyl-6,7-dichloro-1,5-indandiol (Example 5, Step C), (15.6 g., 0.05 mole) in acetone (500 ml.) in an inert atmosphere is added solid sodium hydroxide (12.6 g., 0.25 mole). Chloroform (7.6 g., 0.69 mole) in acetone (50 ml.) is added dropwise during a ten-minute period. The reaction mixture is refluxed for 5 hours, then evaporated to dryness at reduced pressure. The residue is dissolved in water, filtered and acidified with hydrochloric acid affording α,α-dimethyl-(1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. customevaporated to dryness at reduced pressure
  3. dissolutionThe residue is dissolved in water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ddaacc4246174a10807334447264b122
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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