Water → 1,3-Dihydroisobenzofuran

HRID 1156491Notes

Reaction equation

HRID 1156491 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH2:9]Cl)=[CH:5][CH:6]=[CH:7][CH:8]=1.C(=O)(OC)[O:12]C.O>CN(C)C=O>[CH2:2]1[O:12][CH2:9][C:4]2[C:3]1=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 962WaterHCID 119191,2-Bis(chloromethyl)benzeneHCID 12021Dimethyl Carbonate

Product 1

HCID 103271,3-DihydroisobenzofuranYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure described in Example 1 was followed in reacting 0.05 g mole of α,α'-dichloro-o-xylene with 0.06 g mole of dimethyl carbonate in 50 ml of N,N-dimethylformamide. After 22 hours, the reaction mixture was poured into 100 ml of water and the organic portion was extracted from the mixture with three 5050 ml portions of hexane. The combined extracts were dried over MgSO4 and the hexane was distilled off. The residue was distilled under reduced pressure to obtain 2.29 g (37 percent yield) of phthalan (1,3-dihydroisobenzofuran), b.p. 95° C./30 mm.

Workup

  1. extractionthe organic portion was extracted from the mixture with three 5050 ml portions of hexane
  2. dry with materialThe combined extracts were dried over MgSO4
  3. distillationthe hexane was distilled off
  4. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c9f9710e93344869a942a8eeacee934f
Source dataset
uspto-grants-1982_06
Patent number
US04336195

Reaction notes

Loading…