Sodium Hydroxide → 3-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid

HRID 732517ノート

反応式

HRID 732517 の反応式
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:7]([C:8]([O:10]CC)=[O:9])[CH:6]=1)[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1)[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 610139Diethyl 5-(hydroxymethyl)isophthalate

生成物 1

HCID 210858293-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid収率 74.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Add commercially available 5-hydroxymethyl-isophthalic acid diethyl ester (5 g, 19.8 mmol) and NaOH (0.79 g, 19.8 mmol) to ethanol (100 mL). Stir for 4 h at room temperature. Concentrate and pour the residue into water (100 mL) and diethyl ether (100 mL). Separate the aqueous layer and wash it with diethyl ether (40 mL). Acidify the aqueous layer with 5 N HCl to about pH=1. Extract the acidic solution with ethyl acetate (3×40 mL). Wash the combined organic layers with water, saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give the title compound as a solid (3.3 g, 74%).

後処理

  1. concentrationConcentrate
  2. additionpour the residue into water (100 mL) and diethyl ether (100 mL)
  3. customSeparate the aqueous layer
  4. washwash it with diethyl ether (40 mL)
  5. extractionExtract the acidic solution with ethyl acetate (3×40 mL)
  6. washWash the combined organic layers with water, saturated aqueous sodium chloride
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate

出典と根拠

ORDレコード
ord-24aa5fc3c4074e94ac0512758b249ce9
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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