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

HRID 1242478Notes

Reaction equation

HRID 1242478 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ae65bfb14f644be7ae9e4ce3f347432b
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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