Lithium Hydroxide → 4-Carboxymethyl-phenoxy-2-methyl-propionic acid tert-butyl ester

HRID 1242478ノート

反応式

HRID 1242478 の反応式
[C:1]([O:5][C:6](=[O:22])[C:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].OC1C=CC(CC(OC)=O)=CC=1.BrC(C)(C)C(OC(C)(C)C)=O.[Li+].[OH-].Cl.O>O1CCOCC1>[C:1]([O:5][C:6](=[O:22])[C:7]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:15][CH:16]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 5

HCID 3939Lithium HydroxideHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 21885828Hydrate;hydrochlorideHCID 670720912-(4-Methoxycarbonylmethyl-phenoxy)-2-methyl-propionic acid tert-butyl ester

生成物 1

HCID 670720574-Carboxymethyl-phenoxy-2-methyl-propionic acid tert-butyl ester収率 100.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

6.27 g (20.3 mmol) of 2-(4-methoxycarbonylmethyl-phenoxy)-2-methyl-propionic acid tert-butyl ester (prepared from methyl 4-hydroxyphenylacetate and tert-butyl alpha-bromoisobutyrate, in analogy to the procedure described in example 52A]) was dissolved in 100 ml of dioxane; to the stirred solution, 40.7 ml of 1N LiOH solution was added drop by drop. After 30 min., the reaction mixture was poured into crashed ice, the pH was adjusted to <3 with HCl/H2O and it was extracted twice with AcOEt. The combined organic phases were washed with water, dried over anhydrous magnesium sulfate and evaporated to give 6.01 g of the title compound as a light yellow solid.

後処理

  1. additionthe reaction mixture was poured
  2. extractionwas extracted twice with AcOEt
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

出典と根拠

ORDレコード
ord-ae65bfb14f644be7ae9e4ce3f347432b
出典データセット
uspto-grants-2006_10
特許番号
US07115611B2

反応ノート

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