Lithium Hydroxide → 4-Acetaminobenzyl alcohol

HRID 2197954Notes

Reaction equation

HRID 2197954 reaction equation
[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:8]([CH2:9][O:10]C(=O)C)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Li+].[OH-]>C1COCC1>[OH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 187236254-Acetamidobenzyl acetate

Product 1

HCID 1521414-Acetaminobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 197a (4.00 g, 19.3 mmol) in THF (40 mL) was added aqueous LiOH solution (0.91 g, 21.2 mmol dropwise at room temperature over 10 minutes. The mixture was allowed to stir at room temperature for 27 hours and then evaporated. The aqueous residue was diluted with H2O, adjusted to pH 4 with 10% HCl, and then extracted with EtOAc. The extract was washed with brine, dried over MgSO4, filtered and concentrated under vacuum giving the title compound which was purified by washing with cold EtOAc to give the title compound as colorless crystals (2.92 g, 92%).

Workup

  1. customevaporated
  2. additionThe aqueous residue was diluted with H2O
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-04dd3bafb1894f85b9158da71621b707
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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