Methanol → HCID 89580852, compound

HRID 2170476Notes

Reaction equation

HRID 2170476 reaction equation
[CH2:1]([O:5][CH:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)[CH3:7])[CH:2]([CH3:4])[CH3:3].CO.O.[OH-].[Li+]>O1CCCC1>[CH2:1]([O:5][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)[CH3:7])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 89581006HCID 89581006, compound

Product 1

HCID 89580852HCID 89580852, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(1-isobutoxyethyl)benzoate (180 mg, 0.76 mmol) in tetrahydrofuran:methanol:water=3:1:1 (4 mL) was added lithium hydroxide (100 mg, 2.4 mmol). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuum and quenched with aqueous 1N hydrochloric acid (5 mL). The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined extract was dried over sodium sulphate, evaporated and purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give the product 4-(1-isobutoxyethyl)benzoic acid (132 mg, 78%) as pale solid.

Workup

  1. concentrationThe suspension was concentrated in vacuum
  2. customquenched with aqueous 1N hydrochloric acid (5 mL)
  3. extractionextracted with dichloromethane (50 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over sodium sulphate
  6. customevaporated
  7. custompurified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-4f5bdfba22e1405c8e731ec07cc3ee8c
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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