Methyl Salicylate → HCID 21190790, compound

HRID 1068856Notes

Reaction equation

HRID 1068856 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].O[C:8]1C=CC=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Br[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1>CN(C)C=O>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[CH2:19][O:4][C:2]1[CH:3]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:1]=1

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 703202-BromomethylnaphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 21190790HCID 21190790, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3.9 g (35 mmol) of potassium tert-butoxide were added a little at a time to 5 g (33 mmol) of methyl hydroxybenzoate in 200 ml of dimethylformamide. After about 15 min, a further 7.3 g (33 mmol) of 2-(bromomethyl)naphthalene were added and the reaction mixture was heated to 100° C. for about 3 h. The reaction mixture was then poured into ice-water and the product was extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. 8.4 g (88%) of the product were obtained.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-833350f76b0d45298dfe49e0745dfc35
Source dataset
uspto-grants-2001_06
Patent number
US06251917B1

Reaction notes

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