Hydrochloric Acid → HCID 23132783, compound

HRID 2062060Notes

Reaction equation

HRID 2062060 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[C:4]([C:24]([O:26]C)=[O:25])[CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[C:4]([C:24]([OH:26])=[O:25])[CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66701230HCID 66701230, compound

Product 1

HCID 23132783HCID 23132783, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.22 g of 4-fluoro-1-[4-(trifluoromethyl)benzyloxy]-naphthalene-2-carboxylic acid, methyl ester in 4.5 ml of THF and 0.86 ml of methanol was added 1.7 ml of 1M sodium hydroxide. The mixture was stirred at ambient temperature for 11 h. The mixture was diluted with water, acidified to pH 1-2 with 1M HCl, extracted twice with ethyl acetate, dried (sodium sulphate), filtered and concentrated to provide 0.21 g of 4-fluoro-1-[4-(trifluoromethyl)benzyloxy]naphthalene-2-carboxylic acid as a white solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialdried (sodium sulphate)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e139e2d0c474ad8a7e491302074f14b
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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