Hydrochloric Acid → HCID 59544167, compound

HRID 1094652Notes

Reaction equation

HRID 1094652 reaction equation
[OH-].[Na+].[F:3][C:4]([F:23])([F:22])[C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18]([O:20]C)=[O:19])[CH:12]=[CH:11]2)([OH:7])[CH3:6].Cl>CO>[F:3][C:4]([F:22])([F:23])[C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18]([OH:20])=[O:19])[CH:12]=[CH:11]2)([OH:7])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66637142HCID 66637142, compound

Product 1

HCID 59544167HCID 59544167, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a methanol (15 ml) and 2N sodium hydroxide aqueous solution (5 ml), methyl 6-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-naphthoate (3.45 mmol, 1.0 g) was added and the mixture was stirred for 2 hours at 60° C. Then, the reaction mixture was acidified with 2M hydrogen chloride aqueous solution and partitioned with ethyl acetate (50 ml). The organic layer was dried over sodium sulfate and evaporated to give the title compound as a white solid (0.9 g, quant). 1H NMR (300 MHz, CDCl3) δ ppm 1.81 (3H, s), 6.85 (1H, s), 7.70-8.75 (6H, m), 12.94 (1H, br.s).

Workup

  1. custompartitioned with ethyl acetate (50 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-c38b1ec876fd433ea66aeda231d58bd9
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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