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

HRID 21267ノート

反応式

HRID 21267 の反応式
[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]

参加物

5

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 12575Isovanillic AcidHCID 81531Diisopropylethylamine

生成物 1

HCID 653645693-Methoxymethoxy-4-methoxybenzoic acid収率 76.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-68c05f070a0c4065b0fa230829e65713
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

反応ノート

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