Sulfur → Methyl 1-hydroxy-6,7-dimethoxy-2-naphthalenecarboxylate

HRID 1638796Notes

Reaction equation

HRID 1638796 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:17][CH3:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=[O:19])=[O:4].[S]>>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([O:17][CH3:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]=1[OH:19])=[O:4]

Participants

3

Reactant 2

HCID 5362487SulfurHCID 14084378HCID 14084378, compound

Product 1

HCID 14676199Methyl 1-hydroxy-6,7-dimethoxy-2-naphthalenecarboxylateYield 20.2%

Conditions

Temperature
205 °C

Procedure

A mixture of 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthoic acid methyl ester (1.5 g) and powdery sulfur (0.5 g) is heated at 200-210° C. for 2 hours. The reaction mixture is, after cooling, purified by silica gel column chromatography (hexane:ethyl acetate=2:1), followed by crystallization from a mixture of ethyl ether and petroleum ether to afford 6,7-dimethoxy-1-hydroxy-2-napthoic acid methyl ester (0.3 g) as colorless needles, m.p. 144°-145° C.

Workup

  1. temperatureafter cooling
  2. custompurified by silica gel column chromatography (hexane:ethyl acetate=2:1)
  3. customfollowed by crystallization from a mixture of ethyl ether and petroleum ether

Sources & evidence

ORD record
ord-08f573160a0a4c409f8f276c02626fe8
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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