Sodium Hydroxide → HCID 89643934, compound

HRID 1478999Notes

Reaction equation

HRID 1478999 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[O:14][CH2:15][CH3:16])C>CCO>[CH2:15]([O:14][C:8]1[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=1[C:6]([OH:17])=[O:5])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59198761Ethyl 2-ethoxy-4-fluorobenzoate

Product 1

HCID 89643934HCID 89643934, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A 5M solution of sodium hydroxide (6.5 mL; 32.5 mmol; 3 eq.) was added to a solution of 2-ethoxy-4-fluoro-benzoic acid ethyl ester (2.3 g; 10.8 mmol; 1 eq.) in EtOH (46 mL) and the resulting mixture was stirred at 40° C. for 18 hours then concentrated in vacuo. The residue was taken up in water and the pH made acidic with 5M HCl. The precipitate was filtered off, washed with water and dried to afford the title compound (1.8 g, 90%) as a white solid. 1H NMR (DMSO-d6) δ 12.56 (s, 1H), 7.71 (dd, J=7.0, 8.6 Hz, 1H), 7.01 (dd, J=2.4, 11.7 Hz, 1H), 6.80 (dt, J=2.4, 8.5 Hz, 1H), 4.09 (q, J=7.0 Hz, 2H), 1.32 (t, J=7.0 Hz, 3H). HPLC (max plot) 99.3%; Rt 2.71 min. UPLC/MS: (MS+) 185.2 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-6ad420e8bf8241c691c9159890a484ca
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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