Sodium Hydroxide → 1355636-71-3

HRID 508420Notes

Reaction equation

HRID 508420 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 44570902HCID 44570902, compound

Product 1

HCID 666678431355636-71-3Yield 62.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 3-chloro-4-[(3,4-difluorobenzyl)oxy]benzoate (Preparation 10, 10.86 g, 34.7 mmol) in methanol (700 mL) and water (150 mL) was added sodium hydroxide (6.946 g, 173.7 mmol) and the resulting reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, diluted with water (285 mL), adjusted to pH 3 with hydrochloric acid and the resulting precipitate collected by filtration, washed with water and the azeotroped with toluene in vacuo twice to yield the title compound as a solid (6.5 g, 62% over 2 steps).

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water (285 mL)
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed with water
  6. customthe azeotroped with toluene in vacuo twice

Sources & evidence

ORD record
ord-6a988515e77549f9ae67622f88a5706a
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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