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

HRID 842325

Reaction equation

HRID 842325 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].C(Cl)Cl.[C:10]1(C)[CH:15]=[CH:14]C=[CH:12][CH:11]=1.C(C1C=CC=CC=1)C>O.C1(C)C(C)=CC=CC=1>[CH2:5]1[C:6]2[C:12](=[CH:11][CH:10]=[CH:15][CH:14]=2)[CH2:2][C:1](=[O:3])[O:4]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 7500EthylbenzeneHCID 8857Ethyl Acetate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

Recovery of isochromanones after the reaction is possible by concentration of reaction mixture or extraction with organic solvents such as ethyl acetate, methylene chloride, toluene, xylene, and ethylbenzene. Depending on the target isochromanones, when there are two layers, i.e., water layer and product layer, it is possible to separate the water layer and remove it. In particular, when the product is 3-isochromanone, the product layer is liquid at 85° C. or higher, and the solubility in water is low so that the target compound can be recovered by the operation of separation. Further, it is possible to obtain high purity 3-isochromanone by distillation purification under reduced pressure.

Workup

  1. customto separate the water layer
  2. customremove it
  3. customat 85° C.
  4. customcan be recovered by the operation of separation

Sources & evidence

ORD record
ord-08c3f210f5904025865c4c3628dbaab9
Source dataset
uspto-grants-2002_04
Patent number
US06372921B1

Linked notes

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