Sulfur → 6-Butoxy-2-naphthoic acid

HRID 1638780Notes

Reaction equation

HRID 1638780 reaction equation
[CH2:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:16]([OH:18])=[O:17])[CH2:12][CH2:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[S]>C(OCC)C>[CH2:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9](=[CH:8][CH:7]=1)[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[CH:12]=[CH:13]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 146761917-Butoxy-1,2-dihydro-3-naphthoic acid

Product 1

HCID 110211286-Butoxy-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7-butoxy-1,2-dihydro-3-naphthoic acid (0.9 g) and powdery sulfur (0.25 g) is heated at 200°-210° C. for 35 minutes. After cooling, the mixture is dissolved in ethyl ether (200 ml). The solution is extracted with a 0.5N aqueous solution of sodium hydroxide. The aqueous layer is made acid with concentrated hydrochloric acid, and the precipitating crystals are collected by filtration. The crystals are dissolved in acetone, and insolubles are filtered off. The filtrate is concentrated under reduced pressure to allow crystals to precipitate. To the precipitates is added (100 ml), and the precipitates are collected by filtration to afford 6-butoxy-2-naphthoic acid

Workup

  1. temperatureis heated at 200°-210° C. for 35 minutes
  2. temperatureAfter cooling
  3. extractionThe solution is extracted with a 0.5N aqueous solution of sodium hydroxide
  4. filtrationthe precipitating crystals are collected by filtration
  5. dissolutionThe crystals are dissolved in acetone
  6. filtrationinsolubles are filtered off
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customto precipitate
  9. additionTo the precipitates is added (100 ml)
  10. filtrationthe precipitates are collected by filtration

Sources & evidence

ORD record
ord-5a540c3f4ca048999365cff9d3d92094
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

Loading…