Hydrochloric Acid → 1-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid

HRID 1039111Notes

Reaction equation

HRID 1039111 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)=[O:4].[OH-].[Na+].CO.Cl>O>[F:24][C:23]([F:25])([F:26])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][O:15][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:5]=2[C:3]([OH:4])=[O:2])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 688451721-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 688420491-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.59 g of 1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid methyl ester were added 10 ml of 2 M aqueous sodium hydroxide and 10 ml of methanol. After 3 h at reflux the mixture was poured unto water, treated with 2 M hydrochloric acid, and three times extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and concentrated in vacuo. The resulting residue was purified by crystallization from pentane to yield 1.22 g of 1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid.

Workup

  1. temperatureAfter 3 h at reflux the mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by crystallization from pentane

Sources & evidence

ORD record
ord-5941664bf4b04cb7b12291e013085dcf
Source dataset
uspto-grants-2013_10
Patent number
US08552033B2

Reaction notes

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