Hydroxyphenylacetic acid → [(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acid

HRID 899871

反応式

HRID 899871 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]Br>C(O)C>[CH3:14][O:15][C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)=[O:25]

参加物

5

反応物 3

HCID 127Hydroxyphenylacetic acidHCID 14797Potassium HydroxideHCID 2734813Methyl 2-(bromomethyl)benzoate

生成物 1

HCID 68869545[(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acid収率 17.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Hydroxyphenylacetic acid (760 mg, 4.995 mmol) was dissolved in ethanol (99.5%, 20 ml). Potassium hydroxide (560.5 mg, 9.99 mmol) was added. The mixture was stirred at room temperature for 30 minutes. 2-Bromomethylbenzoic acid methyl ester (1144.2 mg, 4.995 mmol) was then dropped in. The resulting mixture was heated to reflux for 2 hours and then evaporated in vacuum to dry. Water and ethyl acetate were added into the residue and the phases were separated. The water phase was acidified with 10% hydrochloric acid, pH˜5, and then extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and evaporated in vacuum to dry. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/6 ml) using DCM, MeOH/DCM (1:99) as eluant gave the desired product (262 mg), yield 17.5%.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customevaporated in vacuum
  4. customto dry
  5. additionWater and ethyl acetate were added into the residue
  6. customthe phases were separated
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried with magnesium sulphate
  9. customevaporated in vacuum
  10. customto dry

出典と根拠

ORDレコード
ord-bfa187513f6b4568a95bd65ebf51f325
出典データセット
uspto-grants-2008_04
特許番号
US07355069B2

関連ノート

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