Chloromethyl Methyl Ether → 3-Methoxymethyloxyphthalic anhydride

HRID 1064833

Reaction equation

HRID 1064833 reaction equation
C(N(CC)C(C)C)(C)C.[OH:10][C:11]1[CH:21]=[CH:20][CH:19]=[C:13]2[C:14]([O:16][C:17](=[O:18])[C:12]=12)=[O:15].[CH3:22][O:23][CH2:24]Cl>ClC(Cl)C>[CH3:22][O:23][CH2:24][O:10][C:11]1[CH:21]=[CH:20][CH:19]=[C:13]2[C:14]([O:16][C:17](=[O:18])[C:12]=12)=[O:15]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl Ether2×HCID 81531Diisopropylethylamine2×HCID 965803-Hydroxyphthalic anhydride

Product 1

HCID 219367353-Methoxymethyloxyphthalic anhydrideYield 99.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

N,N-Diisopropylethylamine (4.39 g, 34.0 mmol) was added to a solution of 3-hydroxyphthalic anhydride (5.0 g, 30.5 mmol) in dichloroethane (60 ml), then chloromethyl methyl ether (2.57 g, 32.0 mmol) was dropped thereinto under cooling with ice water and the mixture was returned to room temperature and stirred for 1 hour. Then N,N-diisopropylethylamine (2.20 g, 17.0 mmol) and chloromethyl methyl ether (1.28 g, 16.0 mmol) were further added thereto followed by stirring for 1 hour. After the reaction, the solvent was evaporated and the residue was diluted with water followed by extracting with ether. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom to provide 6.3 g (yield 99%) of 3-methoxymethyloxyphthalic anhydride as colorless oil.

Workup

  1. customwas returned to room temperature
  2. stirringby stirring for 1 hour
  3. customAfter the reaction
  4. customthe solvent was evaporated
  5. additionthe residue was diluted with water
  6. extractionby extracting with ether
  7. washThe organic layer was washed with water
  8. dry with materiala saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-467e662847c44e3ea5003641010b370c
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Linked notes

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