Lithium Hydroxide → HCID 89581184, compound

HRID 1501257Notes

Reaction equation

HRID 1501257 reaction equation
[OH-].[Li+].[OH:3][CH2:4][CH:5]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1.C1(C)CCC(C(C)C)C(O)C1.O>[OH:3][CH2:4][CH:5]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=1)[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 89581278HCID 89581278, compound

Product 1

HCID 89581184HCID 89581184, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1254MentholSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium hydroxide (400 mg, 10.2 mmol) in tetrahydrofuran, menthol and water (20 mL, 3:1:1, V/V) was added methyl 4-(2-hydroxy-1-phenoxyethyl)benzoate (400 mg, 1.47 mmol). The reaction mixture was stirred at room temperature for 1 hour. The mixture was quenched with 10% HCl (aqueous, 5 mL), extracted with dichloromethane and menthol (60 mL, 10:1), the combine organic layer was dried with anhydrous sodium sulfate, filtered and evaporated to give 4-(2-hydroxy-1-phenoxyethyl)benzoic acid (300 mg, 70%). LCMS (M+H+) m/z: calcd 258.09. found 258

Workup

  1. customThe mixture was quenched with 10% HCl (aqueous, 5 mL)
  2. extractionextracted with dichloromethane and menthol (60 mL, 10:1)
  3. dry with materialthe combine organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a0378773da794941a43a4010b93a837c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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