Toluene → 1,4-dihydro-3H-2-benzopyran-3-one

HRID 842326

Reaction equation

HRID 842326 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].[C:7]1(C)[CH:12]=[CH:11]C=[CH:9][CH:8]=1.C1(C)C(C)=CC=CC=1.C(C1C=CC=CC=1)C>C(Cl)Cl>[CH2:5]1[C:6]2[C:9](=[CH:8][CH:7]=[CH:12][CH:11]=2)[CH2:2][C:1](=[O:3])[O:4]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7237O-XyleneHCID 7500EthylbenzeneHCID 8857Ethyl Acetate

Product 1

HCID 780921,4-dihydro-3H-2-benzopyran-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After the reaction, recovery of isochromanones can be carried out by concentration of reaction mixture or extraction with an organic solvent such as ethyl acetate, toluene, xylene, ethylbenzene, or methylene chloride. When the reaction mixture is separated into two layers, i.e., a water layer and a product layer, depending on the target isochromanones, it is possible to separate and remove the water layer. In particular, when the product is 3-isochromanone, the product layer is liquid at 85° C. or higher, so that solubility in water is low and the target compound can be recovered by separation operation. Further, distillation and purification under reduced pressure can give rise to highly pure 3-isochromanone.

Workup

  1. customWhen the reaction mixture is separated into two layers, i.e.
  2. customto separate
  3. customremove the water layer
  4. customat 85° C.
  5. customthe target compound can be recovered by separation operation
  6. distillationFurther, distillation and purification under reduced pressure

Sources & evidence

ORD record
ord-bdf2f6d3faaf446184656218d3c84c1f
Source dataset
uspto-grants-2002_04
Patent number
US06372921B1

Linked notes

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