Chloromethyl Methyl Ether → 3-Methoxymethyloxyphthalic anhydride

HRID 1242059

Reaction equation

HRID 1242059 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[O:5][C:6]2=[O:11].C(N(C(C)C)CC)(C)C.[CH3:22][O:23][CH2:24]Cl>CN(C)C=O>[CH3:22][O:23][CH2:24][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[O:5][C:6]2=[O:11]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 965803-Hydroxyphthalic anhydride

Product 1

HCID 219367353-Methoxymethyloxyphthalic anhydrideYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-isobenzofuran-1,3-dione (0.5 g, 3.03 mmol) in anhydrous N,N-dimethylformamide (6 ml) under nitrogen was added diisopropylethylamine (1.05 ml, 6.06 mmol). The solution was stirred with cooling in an ice bath and chloromethyl methyl ether (0.46 ml, 6.06 mmol) was added. The reaction was allowed to slowly warm to ambient temperature and then stirred for an additional 7 h. The mixture was concentrated in vacuo to a small volume and diluted with ethyl acetate (75 ml). The organic layer was washed with water (2×40 ml), brine (20 ml), dried (Na2SO4), filtered, and the solvent evaporated in vacuo to give 0.6 g (95%) of 4-methoxymethoxy-isobenzofuran-1,3-dione as a solid.

Workup

  1. temperaturewith cooling in an ice bath
  2. stirringstirred for an additional 7 h
  3. concentrationThe mixture was concentrated in vacuo to a small volume
  4. additiondiluted with ethyl acetate (75 ml)
  5. washThe organic layer was washed with water (2×40 ml), brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9c159aa09fca4c05ba10f78ada78664b
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Linked notes

Loading…