Methyl Ethyl Ketone → 6-Benzyloxynaphthalene-2-carboxylic acid methyl ester

HRID 346082Notes

Reaction equation

HRID 346082 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:16]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7503Benzyl Chloride2×HCID 11430Potassium CarbonateHCID 390995Methyl 6-hydroxy-2-naphthoate

Product 1

HCID 199902746-Benzyloxynaphthalene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 6-hydroxy-2-naphthoate (50 g), benzyl chloride (31.3 g), anhydrous potassium carbonate (100 g) and 2-butanone (350 ml) were stirred and refluxed together for 17 hours. Tlc showed the presence of some unreacted starting material and so a further 5 g benzyl chloride was added and refluxing continued for 3 hours. The product was isolated by pouring into water (1 liter), extracting the aqueous layer with 3×600 ml and 2×350 ml 2-butanone, followed by evaporation to dryness. The residue (65.7 g brown solid) was chromatographed over alumina (330 g) and silica gel (130 g) in dichloromethane, and the product was recrystallised from ethyl acetate (350 ml). Yield 37.3 g (51.6% theory) mpt 148.4°-149.3° C.

Workup

  1. temperaturerefluxed together for 17 hours
  2. temperaturerefluxing
  3. customThe product was isolated
  4. extractionextracting the aqueous layer with 3×600 ml and 2×350 ml 2-butanone
  5. customfollowed by evaporation to dryness
  6. customThe residue (65.7 g brown solid) was chromatographed over alumina (330 g) and silica gel (130 g) in dichloromethane
  7. customthe product was recrystallised from ethyl acetate (350 ml)

Sources & evidence

ORD record
ord-39e7ebfe73164317b1116fd8e2437113
Source dataset
uspto-grants-1991_10
Patent number
US05061399

Reaction notes

Loading…