Water → 2-(4-Bromo-phenyl)-[1,3]dioxolane-2-carboxylic Acid

HRID 1697624Notes

Reaction equation

HRID 1697624 reaction equation
C([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[O:10][CH2:9][CH2:8][O:7]1)=[O:5])C.O.[OH-].[Li+]>O1CCCC1>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:6]2([C:4]([OH:5])=[O:3])[O:7][CH2:8][CH2:9][O:10]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 667720462-(4-Bromo-phenyl)-[1,3]dioxolane-2-carboxylic Acid Ethyl Ester

Product 1

HCID 667718452-(4-Bromo-phenyl)-[1,3]dioxolane-2-carboxylic AcidYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-Bromo-phenyl)-[1,3]dioxolane-2-carboxylic acid ethyl ester (example 346a), 300 mg) in tetrahydrofuran (2 mL) and water (2 mL) was added lithium hydroxide (41 mg) in two portions. The reaction mixture was stirred at room temperature over 2 days then concentrated in vacuo. The residue was acidified to pH=1 with aqueous hydrochloric acid solution (0.1N) extracted with ethyl acetate. The combined organic layer were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo to yield the title compound as a colorless oil (225 mg; 66%). MS (ESI): m/z=271.1 [M−H]−.

Workup

  1. concentrationthen concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f52f5cd273d54a36960122ffd9866e34
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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