Lithium Hydroxide → 4-(4-methoxybenzyloxy) benzoic acid

HRID 990024Notes

Reaction equation

HRID 990024 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Li+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 12648420Methyl 4-[(4-methoxyphenyl)methoxy]benzoate

Product 1

HCID 113344014-(4-methoxybenzyloxy) benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4(4-methoxybenzyloxy)benzoate (12.2 g, 44.8 mmole) in 50 ml 1,4-dioxane was added a solution of lithium hydroxide (2.15 g, 89.6 mmole) and the mixture was stirred overnight at 60° C. The mixture was evaporated under reduced pressure and 5% acetic acid was added. The product was filtered, washed with water and dried. Yield: 10.1 g=87%

Workup

  1. customThe mixture was evaporated under reduced pressure and 5% acetic acid
  2. additionwas added
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-43b0a51eaa1b474ea729521aba121ac4
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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