Sodium Hydroxide → 1-Indanone

HRID 483271

Reaction equation

HRID 483271 reaction equation
C1([CH:7]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:16])C=CC=CC=1.[OH-].[Na+].[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[C:8]1(=[O:16])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3184912-Phenyl-2,3-dihydro-1H-inden-1-one3×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 67351-Indanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Racemic 2-phenylindanone VI is the starting material for the process of the invention. As shown in Step B, indanone VI is directly converted to the methylated intermediate VII containing the (+) and (-) enantiomers by treating indanone VI with methyl halide and an aqueous base (e.g., 50% aqueous sodium hydroxide) in an organic solvent (e.g., toluene) in the presence of a chiral catalyst at a temperature, of about 15° C. The 2-methylated (+) and (-) enantiomer of intermediate VII can then be O-demethylated in the presence of a catalyst (AlCl3) to obtain the optically active intermediate (+) and (-) enantiomer indanone mixture VIII which, in turn, can then be alkylated, hydrolyzed, and acidified to obtain the pure (+) and (-) enantiomers of indenyl-oxy acetic acid I at a yield of about 65-80%.

Workup

  1. additioncontaining the (+) and (-) enantiomers
  2. customof about 15° C

Sources & evidence

ORD record
ord-024eb67fa97c479e94ec1fe1b4611416
Source dataset
uspto-grants-1986_03
Patent number
US04578509

Linked notes

Loading…