Hydroxyphenylacetic acid → (4-Hydroxyphenyl)propanedioic acid

HRID 1389403ノート

反応式

HRID 1389403 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.C([N-]C(C)C)(C)C.[Li+].Cl[C:21]([O:23]CC)=[O:22].Cl>O1CCCC1.O>[C:9]([CH:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:21]([OH:23])=[O:22])([OH:11])=[O:10]

参加物

7

反応物 4

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 2724682Lithium diisopropylamide

生成物 1

HCID 3017479(4-Hydroxyphenyl)propanedioic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

About 0.5 mole of 4-hydroxybenzeneacetic acid is dissolved in about 50 ml of anhydrous tetrahydrofuran at -40° C. To this solution is added 3 equivalents of lithium diisopropylamide. The temperature is maintained at about -40° C. for about 15 minutes. Then 1 equivalent of ethyl chloroformate is added and the temperature is raised from about -40° C. to about 20° C. and the reaction mixture stirred for about 60 minutes. The reaction mixture is poured into water and the monoester of α-carboxy-4-hydroxybenzeneacetic acid is recovered from the aqueous solution. Hydrolysis of the half-ester with sodium hydroxide followed by acidification with hydrochloric acid gives α-carboxy-4-hydroxybenzeneacetic acid.

後処理

  1. temperaturethe temperature is raised from about -40° C. to about 20° C.
  2. customthe monoester of α-carboxy-4-hydroxybenzeneacetic acid is recovered from the aqueous solution
  3. customHydrolysis of the half-ester with sodium hydroxide

出典と根拠

ORDレコード
ord-adc763570d5144028f4ae482436b039a
出典データセット
uspto-grants-1981_01
特許番号
US04244885

反応ノート

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