Potassium Carbonate → [[7-(2-Propenyloxy)-2-naphthalenyl]oxy]acetic acid methyl ester

HRID 1719420Notes

Reaction equation

HRID 1719420 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([OH:15])=[CH:12]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>CC(C)=O>[CH3:27][O:26][C:24](=[O:25])[CH2:23][O:15][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][CH:7]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 111716387-(2-Propenyloxy)-2-naphthalenol

Product 1

HCID 13504790[[7-(2-Propenyloxy)-2-naphthalenyl]oxy]acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7.9 g of 7-(2-propenyloxy)-2-naphthalenol and 8.3 g of potassium carbonate in 50 ml of anhydrous acetone was stirred at room temperature for 1.5 hours. Methyl bromoacetate (4.7 ml) was added and stirring was continued for 18 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield (8.4 g) of [[7-(2-propenyloxy)-2-naphthalenyl]oxy]acetic acid methyl ester, mp 69°-70° after recrystallization from ether-hexane.

Workup

  1. stirringstirring
  2. waitwas continued for 18 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-673b2ab29fa94bdd84bfa460d4d30862
Source dataset
uspto-grants-1985_09
Patent number
US04539419

Reaction notes

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