Lithium hydroxide, monohydrate → HCID 59371290, compound

HRID 2095342Notes

Reaction equation

HRID 2095342 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][CH2:6][O:7][CH2:8][C:9]([O:11]C(C)(C)C)=[O:10].O[Li].O>C1COCC1.CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][CH2:6][O:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59371325HCID 59371325, compound

Product 1

HCID 59371290HCID 59371290, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of tert-butyl 2-(3-bromophenethoxy)acetate (580 mg, 1.84 mmol) in THF/CH3OH/H2O (8/4/4 mL) was added LiOH.H2O (232 mg, 5.5 mmol, 3.0 equiv.) at room temperature. The reaction mixture was stirred for 2 h at room temperature. After concentration under vacuum, the pH of the residual solution was adjusted to 2 with 1M hydrochloric acid. The carboxylic acid was extracted into EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford 2-(3-bromophenethoxy)acetic acid (470 mg, 99%) as a colorless oil.

Workup

  1. concentrationAfter concentration under vacuum
  2. extractionThe carboxylic acid was extracted into EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-329794da8fe245f49e800d7b828622e9
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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