Sodium Hydroxide → 3-(methoxymethyl)benzoic Acid

HRID 273096ノート

反応式

HRID 273096 の反応式
[OH-].[Na+].C[O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][CH3:14])[CH:7]=1>CO.O1CCCC1>[CH3:14][O:13][CH2:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:5]([OH:15])=[O:4]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 23080888Methyl 3-(methoxymethyl)benzoate

生成物 1

HCID 49623543-(methoxymethyl)benzoic Acid収率 99%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

1 N Sodium hydroxide (3.6 ml, 3.6 mmol) was added to a 3-methoxymethyl-benzoic acid methyl ester (436 mg, 2.4 mmol) in methanol (5 ml) and tetrahydrofuran (5 ml). The reaction was stirred at 70° C. for 30 min. and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH about 2) by the addition of 1 N HCl (aq.). Following extraction of the aqueous layer with ethyl acetate, the organic layer was then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 395 mg (98%) of 3-methoxymethyl-benzoic acid as a white solid. 1H NMR (DMSO), δ (ppm): 7.90 (s, 1H), 7.87 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H), 4.48 (s, 2H), 3.31 (s, 3H).

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. additionby the addition of 1 N HCl (aq.)
  4. extractionextraction of the aqueous layer with ethyl acetate
  5. washthe organic layer was then washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-5be80a9ee9834ab5aff3f04d49d58be5
出典データセット
uspto-grants-2008_11
特許番号
US07456200B2

反応ノート

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