Methanol → 3-Methoxyphthalic acid

HRID 41454

反応式

HRID 41454 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:5]([C:6]([O:8]C)=[O:7])[C:4]=1[C:13]([O:15]C)=[O:14].[OH-].[K+].CO>O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[C:13]([OH:15])=[O:14]

参加物

5

反応物 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 316224Dimethyl 3-methoxyphthalate

生成物 1

HCID 3152183-Methoxyphthalic acid収率 84%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc., Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 50° C. overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197.

後処理

  1. temperatureat reflux for 4 hours
  2. customwas removed in vacuo
  3. additionthe mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid
  4. customevaporated gently in vacuo
  5. customcrystallization
  6. filtrationThe solid material was filtered off
  7. washwashed with a little ice
  8. temperaturecooled water
  9. customsucked dry under reduced pressure
  10. customdried in a vacuum oven at 50° C. overnight

出典と根拠

ORDレコード
ord-8470350f66824577a068d2eb7336fe7c
出典データセット
uspto-grants-2013_09
特許番号
US08530469B2

関連ノート

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