Chloromethyl Methyl Ether → 3-Methoxymethoxy-4-methoxybenzoic acid

HRID 21267

Reaction equation

HRID 21267 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[C:4]([OH:5])[CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:22][O:23][CH2:24]Cl>ClCCl>[CH3:22][O:23][CH2:24][O:5][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:6]=1[O:7][CH3:8])[C:1]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 12575Isovanillic AcidHCID 81531Diisopropylethylamine

Product 1

HCID 653645693-Methoxymethoxy-4-methoxybenzoic acidYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 347, isovanillic acid (5.00 g, 29.7 mmol) was suspended in dichloromethane (100 mL), and the suspension was treated with diisopropylethylamine (22.8 mL, 131 mmol) and chloromethyl methyl ether (4.96 mL, 65.4 mmol). The solvent was evaporated under reduced pressure. The residue was dissolved in methanol (50 mL) and treated with 4 mol/L aqueous potassium hydroxide solution (50 mL). The solvent was evaporated under reduced pressure. The residue was added with 4 mol/L hydrochloric acid. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 3-methoxymethoxy-4-methoxybenzoic acid (4.82 g, yield 76%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (50 mL)
  3. additiontreated with 4 mol/L aqueous potassium hydroxide solution (50 mL)
  4. customThe solvent was evaporated under reduced pressure
  5. additionThe residue was added with 4 mol/L hydrochloric acid
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water
  8. customby drying under reduced pressure

Sources & evidence

ORD record
ord-68c05f070a0c4065b0fa230829e65713
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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