Ethanol → 2-(7-Methoxynaphthalen-1-yl)acetic acid

HRID 572697Notes

Reaction equation

HRID 572697 reaction equation
[OH-].[Na+].C(O)C.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[C:15]2[CH2:18][C:19]([O:21]CC)=[O:20])=[CH:10][CH:9]=1>O>[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[C:15]2[CH2:18][C:19]([OH:21])=[O:20])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13570063Ethyl (7-methoxynaphthalen-1-yl)acetate

Product 1

HCID 135701052-(7-Methoxynaphthalen-1-yl)acetic acidYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40 g sodium hydroxide was dissolved in 1000 ml water and 1000 ml 95% ethanol was added. They were mixed. Then, 50 g ethyl (7-methoxy-1-naphthyl)-acetate was added into above-mentioned mixture solution and the mixture solution was stirred for 3 hours at room temperature. The reaction was subsequently stopped and vacuum evaporated to remove ethanol, resulting in brown-red liquid. The liquid was washed with 300 ml×2 ethyl acetate prior to adding 30 ml 95% ethanol into the aqueous layer. The pH was adjusted to 2 by adding concentrated hydrochloric acid in drops with rapid stirring, resulting in a large amount of light brown solid being precipitated. They were filtered and dried to obtain 32 g product with mp of 154-156° C. The content measured by HPLC is 98.48%, and the yield is 72%.

Workup

  1. additionThey were mixed
  2. customvacuum evaporated
  3. customto remove ethanol
  4. customresulting in brown-red liquid
  5. washThe liquid was washed with 300 ml×2 ethyl acetate
  6. additionto adding 30 ml 95% ethanol into the aqueous layer
  7. additionby adding concentrated hydrochloric acid in drops with rapid stirring
  8. customresulting in a large amount of light brown solid being
  9. customprecipitated
  10. filtrationThey were filtered
  11. customdried

Sources & evidence

ORD record
ord-a2e77d7e0f5744888f2af008f7f3cf12
Source dataset
uspto-grants-2015_05
Patent number
US09029420B2

Reaction notes

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