Trifluoroacetic anhydride → [1-Oxo-2-(3-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

HRID 1447701

Reaction equation

HRID 1447701 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([Cl:17])[C:15]=1[Cl:16])[C:12](=[O:18])[C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:19])[CH2:10]2)C.[Pb]=O.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:32]>FC(F)(F)C(O)=O>[O:18]=[C:12]1[C:13]2[C:9](=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:3])=[O:26])=[C:15]([Cl:16])[C:14]=2[Cl:17])[CH2:10][C:11]1([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([OH:32])[CH:25]=1)[CH3:19]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 14827Lead monoxideHCID 20384378Ethyl(1-oxo-2-phenyl-2-methyl-6,7-dichloro-5-indanyloxy)acetate

Product 1

HCID 20378235[1-Oxo-2-(3-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acidYield 60%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
25 °C

Procedure

Ethyl(1-oxo-2-phenyl-2-methyl-6,7-dichloro-5-indanyloxy)acetate (18.95 g., 0.05 mole) dissolved in trifluoroacetic acid (100 ml.) is added portionwise at less than 10° C. to a stirred mixture of lead tetrakistrifluoroacetate (0.055 mole) prepared by stirring lead oxide (37.5 g.), trifluoroacetic acid (85 ml.) and trifluoroaceticanhydride (75 g.) at 25° C. for 96 hrs. After stirring the reaction mixture at 25° C. for 6 hours it is poured into crushed ice-water (1 l.) to precipitate 19.7 g. of a mixture of esters which is hydrolyzed by heating at reflux with ethanol (400 ml.) -water (250 ml.)-10 N sodium hydroxide solution (40 ml.) for 3/4 hr. On addition to crushed ice-water (1 l.)-12 N hydrochloric acid (50 ml.) a gummy product precipitates, is extracted with ether then concentrated to give 60% of [1-oxo-2-(3-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid and 20% of the 4-hydroxyphenyl derivative. Crystallization from acetic acid gives 2.6 g. of [1-oxo-2-(3-hydroxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid, m.p. 248°-255° C.

Workup

  1. customprepared
  2. additionis poured
  3. customto precipitate 19.7 g
  4. additionof a mixture of esters which
  5. temperatureby heating
  6. temperatureat reflux with ethanol (400 ml.) -water (250 ml.)-10 N sodium hydroxide solution (40 ml.) for 3/4 hr
  7. additionOn addition
  8. customto crushed ice-water (1 l.)-12 N hydrochloric acid (50 ml.) a gummy product
  9. customprecipitates
  10. extractionis extracted with ether
  11. concentrationthen concentrated

Sources & evidence

ORD record
ord-5fcf14918425455ab8bd1821fb001ae8
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Linked notes

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