Sodium Hydroxide → 3,5-Dichloro-4-isopropoxybenzoic acid

HRID 1820967

Reaction equation

HRID 1820967 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:16])[C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:16])[C:11]=1[O:12][CH:13]([CH3:14])[CH3:15])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58438776HCID 58438776, compound

Product 1

HCID 670818343,5-Dichloro-4-isopropoxybenzoic acidYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.88 g (7.15 mmol) of methyl 3,5-dichloro-4-isopropoxybenzoate (from Step A) in 20 mL of methanol was added 4 mL of 5.0 N sodium hydroxide solution. The mixture was stirred at rt overnight and concentrated. The residue was partitioned between EtOAc (30 mL) and 1 N NaOH (30 mL). The aqueous layer was separated, washed with EtOAc (2×30 mL), acidified using 5.0 N HCl until pH=1, and then extracted with EtOAc (3×30 mL). Organic layers were combined, dried over MgSO4, and concentrated to give 1.51 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.43 (d, J=6.2, 6H), 4.79 (m, 1H), 8.07 (s, 2H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between EtOAc (30 mL) and 1 N NaOH (30 mL)
  3. customThe aqueous layer was separated
  4. washwashed with EtOAc (2×30 mL)
  5. extractionextracted with EtOAc (3×30 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e518055aded2439fb41c1f6f7571f675
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Linked notes

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