Sodium Hydroxide → HCID 89650782, compound

HRID 1479003Notes

Reaction equation

HRID 1479003 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[O:13][C:14]([F:19])([F:18])[CH:15]([F:17])[F:16]>CO>[F:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]([OH:20])=[O:4])=[C:7]([O:13][C:14]([F:18])([F:19])[CH:15]([F:17])[F:16])[CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89650354HCID 89650354, compound

Product 1

HCID 89650782HCID 89650782, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5N aqueous solution of NaOH (1.96 mL, 9.82 mmol) was added into a solution of 4-fluoro-2-(1,1,2,2-tetrafluoro-ethoxy)-benzoic acid methyl ester (884 mg, 3.27 mmol) in MeOH (10 mL). The resulting mixture was stirred at RT for 15 hours, then concentrated under vacuum. The residue was taken up with water (20 mL) and acidified until pH=1 with a 1N aqueous solution of HCl. The precipitate was filtered off, washed with water (3×) and dried under vacuum to give the title compound as a white powder (661 mg, 79%). 1H NMR (300 MHz, DMSO-d6) δ 13.38 (s, 1H), 8.02-7.93 (m, 1H), 7.43-7.32 (m, 2H), 6.73 (tt, J=51.7, 3.5 Hz, 1H). HPLC (max plot) 96.8%; Rt 3.72 min. UPLC/MS: (MS−) 255.2 ([M−H]−).

Workup

  1. concentrationconcentrated under vacuum
  2. filtrationThe precipitate was filtered off
  3. washwashed with water (3×)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-29373070ede14c4c83d8c0cd4afea8f4
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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