Ethanol → HCID 15614955, compound

HRID 620368Notes

Reaction equation

HRID 620368 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([C:15]([F:18])([F:17])[F:16])[C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[F:19].C([O-])=[O:21].[Na+].C(O)C>O>[F:19][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=2[C:15]([F:18])([F:17])[F:16])[C:3]=1[CH2:2][OH:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723810Sodium FormateHCID 15614954HCID 15614954, compound

Product 1

HCID 15614955HCID 15614955, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 1-bromomethyl-2-fluoro-6-methoxy-5-(trifluoromethyl)naphthalene (11.16 g, 35 mmol), sodium formate (5.85 g, 86 mmol), ethanol (134 mL) and water (34 mL) was heated to reflux with stirring. Dissolution occurred with 20 minutes. After 1.5 hours the heating source was removed, 2.5N NaOH (14mL) was added, and the reaction mixture was cooled to room temperature. The ethanol was removed, water (100 mL) was added and the solid was filtered. The white solid was washed with water and dried in vacuo to give the product in quantitative yield. A small portion was recrystallized from petroleum ether:ethyl acetate, m.p. 113°-114° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. dissolutionDissolution
  4. customAfter 1.5 hours the heating source was removed
  5. addition2.5N NaOH (14mL) was added
  6. customThe ethanol was removed
  7. additionwater (100 mL) was added
  8. filtrationthe solid was filtered
  9. washThe white solid was washed with water
  10. customdried in vacuo
  11. customto give the product in quantitative yield
  12. customA small portion was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-d0ec43b1c61e49e0b28baf31613ba22e
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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