Sodium Hydroxide → RP-101124

HRID 1820960Notes

Reaction equation

HRID 1820960 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[Na+]>CCO>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21956805Methyl 3-cyano-4-isopropoxybenzoate

Product 1

HCID 21956832RP-101124Yield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 802 mg (3.66 mmol) of methyl 3-cyano-4-isopropyloxybenzoate (from Step C) in 5.0 mL EtOH was treated with 770 μL of 5.0 N NaOH. The mixture was stirred at rt for 16 h and then concentrated. The residue was partitioned between EtOAc and aqueous HCl. The organic layer was separated, dried over Na2SO4, and concentrated to give 706 mg of the title compound: 1H NMR (500 M, CDCl3) δ 1.46 (d, J=6.0, 6H), 4.74-4.81 (m, 1H), 7.02 (d, J=9.0, 1H), 8.24 (dd, J=2.3, 8.9, 1H), 8.32 (d, J=2.0, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between EtOAc and aqueous HCl
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0a2db9b4eb444b62a1537e7924134c12
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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