Ethanol → Ethyl 6-hydroxy-2-naphthoate

HRID 1790187Notes

Reaction equation

HRID 1790187 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]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH2:15](O)[CH3:16]>S(=O)(=O)(O)O>[CH2:15]([O:13][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([OH:1])[CH:3]=2)[CH:8]=1)=[O:14])[CH3:16]

Participants

4

Reactant 2

HCID 702EthanolHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 2769636Ethyl 6-hydroxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6-hydroxy-2-naphthoic acid (75.9 g, 0.40 mol) in ethanol (1.0 L) and sulfuric acid (5.0 mL) was heated to reflux under an atmosphere of nitrogen. After 16 hours, the volume was removed to approximately half via simple distillation and the resulting solution was diluted with water. The resulting cloudy mixture was extracted with EtOAc (4×) and the combined organics were successively washed with NaHCO3 (0.25 M, twice), water, brine and dried (MgSO4). The mixture was filtered and evaporated to give 6-hydroxy-naphthalene-2-carboxylic acid ethyl ester, 85.4 g (98%).

Workup

  1. temperatureto reflux under an atmosphere of nitrogen
  2. customthe volume was removed to approximately half via simple distillation
  3. additionthe resulting solution was diluted with water
  4. extractionThe resulting cloudy mixture was extracted with EtOAc (4×)
  5. washthe combined organics were successively washed with NaHCO3 (0.25 M
  6. dry with materialtwice), water, brine and dried (MgSO4)
  7. filtrationThe mixture was filtered
  8. customevaporated

Sources & evidence

ORD record
ord-5f1461830198416ea9317c089d13033f
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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