Benzyl Chloride → HCID 14773084, compound

HRID 1723352

Reaction equation

HRID 1723352 reaction equation
[Na].[OH:2][C:3]1[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([OH:13])[CH:9]=[CH:8][CH:7]=2.[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([O:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]=[C:3]([OH:2])[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 5360545SodiumHCID 14773083Ethyl 3,5-dihydroxynaphthalene-2-carboxylate

Product 1

HCID 14773084HCID 14773084, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 7.8 g (0.34 g atom) of sodium in 1,000 cc of ethanol, was added 85 g (0.37 mole) of ethyl 3,5-dihydroxy-2-naphthoate. After one-half hour 47 g (0.37 g mole) of benzyl chloride was added. The reaction mixture was warmed under reflux for 24 hours. The hot reaction mixture was filtered and cooled in an ice bath. A tan solid precipitated out, which was filtered off yielding 15.0 g (m.p. 98°-115° C.) of the crude product. Recrystallization first from ethanol and then from acetonitrile furnished ethyl 5-benzyloxy-3-hydroxy-2-naphthoate, m.p. 112° C.-114° C. in 7 percent yield (7.3 g).

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureunder reflux for 24 hours
  3. filtrationThe hot reaction mixture was filtered
  4. temperaturecooled in an ice bath
  5. customA tan solid precipitated out
  6. filtrationwhich was filtered off
  7. customyielding 15.0 g (m.p. 98°-115° C.) of the crude product
  8. customRecrystallization first from ethanol

Sources & evidence

ORD record
ord-b55fcd8880934161831bc32f69c435ff
Source dataset
uspto-grants-1989_08
Patent number
US04861795

Linked notes

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