Hydrochloric Acid → Methyl 6-hydroxy-2-naphthoate

HRID 550199Notes

Reaction equation

HRID 550199 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.Cl.CO.[CH3:18]COC(C)=O>COC(OC)(C)C>[CH3:18][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]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8857Ethyl AcetateHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 390995Methyl 6-hydroxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

Treat a mixture of 6-hydroxy-2-naphthoic acid (4.45 g, 23.6 mmol) in 2,2-dimethoxypropane (235 mL) with conc. HCl (24 mL) and then MeOH (60 mL). Stir the reaction at RT for 16 h and then at 55° C. for 16 h. Pour the reaction mixture into EtOAc (250 mL) and wash with brine (3×100 mL). Dry the organic layer over Na2SO4, concentrate the filtrate, and chromatograph the concentrated filtrate (0.5 kg silica gel, 5:95 to 15:85 EtOAc:hex) to give the title compound (4.77 g, quant). MS (ES) m/e 203 (M+1).

Workup

  1. additionTreat
  2. customthe reaction at RT for 16 h
  3. washwash with brine (3×100 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. concentrationconcentrate the filtrate, and chromatograph the concentrated filtrate (0.5 kg silica gel, 5:95 to 15:85 EtOAc:hex)

Sources & evidence

ORD record
ord-eb5ae362358248e291185f05ac8fc2b4
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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