2-Naphthalenecarboxylic acid, 1-hydroxy-, methyl ester → Methyl 1-(2,2,2-trifluoroethoxy)naphthalene-2-carboxylate

HRID 1973186Notes

Reaction equation

HRID 1973186 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].FC(F)(F)S(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O.C(=O)(O)[O-].[K+]>CC(C)=O>[F:24][C:23]([F:26])([F:25])[CH2:22][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516893Potassium Bicarbonate

Product 1

HCID 21493172Methyl 1-(2,2,2-trifluoroethoxy)naphthalene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture containing 20.2 g. (0.1 mole) of methyl 1-hydroxy-2-naphthoate, 29 g. (0.125 mole) of 2,2,2-trifluoroethyl trifluoromethanesulfonate, 20 g. (0.2 mole) of anhydrous potassium bicarbonate and 200 ml. of dry acetone is refluxed for three days. Acetone is removed by distillation (steam bath). The residue is cooled and diluted with water. The resulting white solid is collected by filtration and washed successively with cold dilute sodium hydroxide solution and water. The solid is further purified by several rcrystallizations from aqueous alcohol followed by sublimation, (oil bath, 60°-75°/0.2 mm. Hg.) to give white solid, m.p. 69.5°-70.5°.

Workup

  1. additionA mixture containing 20.2 g
  2. customAcetone is removed by distillation (steam bath)
  3. temperatureThe residue is cooled
  4. additiondiluted with water
  5. filtrationThe resulting white solid is collected by filtration
  6. washwashed successively with cold dilute sodium hydroxide solution and water
  7. customThe solid is further purified by several rcrystallizations from aqueous alcohol
  8. customfollowed by sublimation, (oil bath, 60°-75°/0.2 mm. Hg.)
  9. customto give white solid, m.p. 69.5°-70.5°

Sources & evidence

ORD record
ord-faf3673942ae46eb85af04f56f77fc09
Source dataset
uspto-grants-1976_12
Patent number
US03996280

Reaction notes

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