Lithium Hydroxide → 4-(2-Methoxypropan-2-yl)benzoic acid

HRID 395732Notes

Reaction equation

HRID 395732 reaction equation
[CH3:1][O:2][C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[OH-].[Li+]>O1CCCC1.CO.C(OCC)C>[CH3:1][O:2][C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 181744854-(1-Methoxy-1-methyl-ethyl)-benzoic acid methyl ester

Product 1

HCID 181744324-(2-Methoxypropan-2-yl)benzoic acidYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(1-methoxy-1-methylethyl)benzoate (120 mg, 0.57 mmol) in tetrahydrofuran (6 mL) and methanol (2 mL) was added 1 M aqueous lithium hydroxide (2 mL). After stirring for 2 h, the reaction mixture was diluted with diethyl ether and washed with 1 N hydrochloric acid (4 mL) and water (4 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo to give 93 mg (84%) of the title compound.

Workup

  1. washwashed with 1 N hydrochloric acid (4 mL) and water (4 mL)
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67c9174a20dd4b938a98bd584a0d709b
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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