Lithium Hydroxide → HCID 67078824, compound

HRID 1501255Notes

Reaction equation

HRID 1501255 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([O:13]C)=[O:12])=[CH:6][CH:5]=1>O1CCCC1.C1(C)CCC(C(C)C)C(O)C1.O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 89581335HCID 89581335, compound

Product 1

HCID 67078824HCID 67078824, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1254MentholSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium hydroxide (3.5 g, 0.042 mmol) in tetrahydrofuran, menthol and water (120 mL, 3:1:1) was added methyl 2-(4-bromophenyl)-2-phenoxyacetate (6.8 g, 0.021 mol). The reaction mixture was stirred at room temperature for 1 hour. The mixture was quench with 10% hydrochloric acid (aqueous, 5 mL), extracted with dichloromethane and menthol (10:1), the combine organic layer was dried with anhydrous sodium sulfate, filtered and evaporated to give 2-(4-bromophenyl)-2-phenoxyacetic acid (6 g, 80%). 1H NMR (300 MHz, DMSO-d6): δ 7.68-7.65 (m, 5H), 7.52-7.49 (m, 2H), 6.88-6.86 (m, 2H), 5.35-5.31 (m, 1H).

Workup

  1. customThe mixture was quench with 10% hydrochloric acid (aqueous, 5 mL)
  2. extractionextracted with dichloromethane and menthol (10:1)
  3. dry with materialthe combine organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-04192361599047459203980965c5044e
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…