Water → Methyl 3-methoxymethoxy-2-naphthoate

HRID 862065

Reaction equation

HRID 862065 reaction equation
[OH:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].[CH3:18][O:19][CH2:20]Cl.O>C1COCC1>[CH3:18][O:19][CH2:20][O:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 70163Methyl 3-hydroxy-2-naphthoate

Product 1

HCID 53900226Methyl 3-methoxymethoxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-hydroxy-2-naphthoate (7.01 g) in THF (200 ml) was cooled to 0° C., to which was added 60% sodium hydride (1.58 g) during 10 minutes. Then, the mixture was stirred for one hour at room temperature, to which was added dropwise chloromethyl methyl ether (2.8 ml). The mixture was then stirred for two hours, to which was added water to quench the reaction, followed by extraction with ethyl acetate. The organic layer was dried (anhydrous magnesium sulfate), and distilled off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give methyl 3-methoxymethoxy-2-naphthoate (7.11 g) (Compound B-19). The physical properties are shown in Table 7.

Workup

  1. stirringThe mixture was then stirred for two hours, to which
  2. customto quench
  3. customthe reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  6. distillationdistilled off the solvent under reduced pressure
  7. customThe residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-41bd6cd5a004418aa0a9fd034ac769b7
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Linked notes

Loading…