Water → Methyl 6-hydroxy-2-naphthoate

HRID 490692Notes

Reaction equation

HRID 490692 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15]C)[CH:11]=2)[CH:6]=1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3].C(S)C.O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 604020Methyl 6-methoxy-2-naphthoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 390995Methyl 6-hydroxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-naphthalene-2-carboxylic acid methyl ester (0.68 g, 3.13 mmol) is stirred in dichloromethane (50 mL) in an ice/water bath. Aluminum trichloride (1.67 g, 12.5 mmol) is added followed by ethane thiol (1.2 mL, 15.7 mmol). The mixture is stirred at room temperature 2 hr. Water (25 mL) is added and the product is extracted into ethyl acetate (2×75 mL). The combined extracts are concentrated, and the residue is purified via silica gel chromatography eluting with 8:2 hexanes:ethyl acetate to afford the title compound as a white solid, 0.432 g, 69%. MS M++1 203. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. extractionthe product is extracted into ethyl acetate (2×75 mL)
  2. concentrationThe combined extracts are concentrated
  3. customthe residue is purified via silica gel chromatography
  4. washeluting with 8:2 hexanes

Sources & evidence

ORD record
ord-799aa5f7ef4a4b6982c00e8e863e2cb5
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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