Methanol → HCID 69669734, compound

HRID 2367902Notes

Reaction equation

HRID 2367902 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][CH2:22][O:23][CH:24]=[CH2:25].CO>O1CCOCC1.C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:25][CH2:24][O:23][CH:22]=[CH2:21])=[O:13]

Participants

7

Reactant 4

HCID 887MethanolHCID 71232-Naphthoic acidHCID 80742-Chloroethyl vinyl etherHCID 11430Potassium Carbonate

Product 1

HCID 69669734HCID 69669734, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In a 300 mL three necked oven dried round bottom flask equipped with a magnetic stirrer, 25 g (0.145 mol) of 2-naphthoic acid and 24.07 g (0.17 mol) of potassium carbonate (K2CO3) were suspended in 100 ml of dioxane and the mixture stirred at room temperature for 1 hour, forming a thick slurry. 18.53 g (0.17 mol) of 2-chloroethylvinyl ether dissolved in 10 ml of dioxane was slowly added to the reaction mixture using a dropping funnel over a period of 1 hour and the reaction refluxed overnight for another 12 hours until a complete reaction was ascertained by thin layer chromatography (TLC) analysis (silica plates; eluant 1% (v/v) methanol in chloroform). The reaction was quenched by pouring the mixture slowly into 400 ml of 0.01% (v/v) hydrochloric acid (HCl) solution, the crude product was extracted into 300 ml of ethyl acetate, and the ethyl acetate extract was washed sequentially with water and brine to neutral pH. The ethyl acetate extracts were then dried over sodium sulfate, filtered and concentrated by rotary evaporation to afford 32 g (92% yield) of an amber oil which solidifies upon standing. The product was used without further purification. 1H NMR (500 MHz, Acetone-d6): δ 8.64 (s, 1H), 8.08 (d, 2H, 8 Hz), 7.89 (d, 2H, 8.5 Hz), 7.64-7.59 (q, 2H), 6.56-6.52 (d/d, 1H, 7 Hz), 5.58 (s, 1H), 4.60 (m, 2H), 4.49 (m, 2H), 2.30 (s, 3H), 1.90 (s, 3H). 13C NMR (125 MHz, CDCl3): δ 166.6, 151.5, 135.6, 132.4, 131.3, 129.4, 128.3, 128.1, 127.7, 127.0, 126.6, 125.2, 87.1, 65.9, 63.3.

Workup

  1. dry with materialIn a 300 mL three necked oven dried round bottom flask
  2. customequipped with a magnetic stirrer
  3. customforming a thick slurry
  4. additionwas slowly added to the reaction mixture
  5. customof 1 hour
  6. temperaturethe reaction refluxed overnight for another 12 hours until a complete reaction
  7. customThe reaction was quenched
  8. additionby pouring the mixture slowly into 400 ml of 0.01% (v/v) hydrochloric acid (HCl) solution
  9. extractionthe crude product was extracted into 300 ml of ethyl acetate
  10. extractionthe ethyl acetate extract
  11. washwas washed sequentially with water and brine to neutral pH
  12. dry with materialThe ethyl acetate extracts were then dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-5eb3df8564dd4586b9e52e9bae50f68c
Source dataset
uspto-grants-2014_04
Patent number
US08703383B2

Reaction notes

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