Lithium Hydroxide → 4-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid

HRID 521430Notes

Reaction equation

HRID 521430 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[CH:5]=1.[OH-].[Li+]>O1CCOCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][C:6]=1[O:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 670765654-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester

Product 1

HCID 670766394-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound of step 1 (0.50 g, 1.43 mmol) was dissolved in dioxane (5 ml), lithium hydroxide (7.1 ml of an aqueous 1 M (i.e. 1 mol per liter) solution) was added, and the mixture was reacted overnight. The mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase extracted with EA, and the organic extracts were dried over sodium sulfate, filtered and evaporated to dryness in vacuo to give 0.414 g of the title compound.

Workup

  1. customthe mixture was reacted overnight
  2. customThe mixture was partitioned between 2 N hydrochloric acid and EA
  3. extractionthe aqueous phase extracted with EA
  4. dry with materialthe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5ed866ff68764d0bb8ea0c50c8211d2b
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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