Water → Ethyl 2,6-dichloro-3-(methoxymethoxy)benzoate

HRID 1604534Notes

Reaction equation

HRID 1604534 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:14]([OH:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:17][O:18][CH2:19]Cl.O>CN(C)C=O>[Cl:3][C:4]1[C:14]([O:15][CH2:17][O:18][CH3:19])=[CH:13][CH:12]=[C:11]([Cl:16])[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 19603351Ethyl 2,6-dichloro-3-hydroxybenzoate

Product 1

HCID 19603256Ethyl 2,6-dichloro-3-(methoxymethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 474 mg) in N,N-dimethylformamide (2 ml) was added a solution of ethyl 2,6-dichloro-3-hydroxybenzoate (2.42 g) in N,N-dimethylformamide (10 ml) under nitrogen at ambient temperature and the mixture was stirred for 1 hour at the same temperature. Chloromethyl methyl ether (1.15 ml) was added thereto and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:8, V/V) to give ethyl 2,6-dichloro-3-(methoxymethoxy)benzoate (2.58 g) as an oil.

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:8, V/V)

Sources & evidence

ORD record
ord-ceab0c19b0034e16a2fe4dcbf52d55ac
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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