Methyl Acrylate → HCID 20716712, compound

HRID 1872310Notes

Reaction equation

HRID 1872310 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=[CH2:15].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2](/[CH:15]=[CH:14]/[C:13]([O:17][CH3:18])=[O:16])[CH:11]=[CH:10]2

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 271446-Bromo-2-naphthalenolHCID 80271Tri-o-tolylphosphine

Product 1

HCID 20716712HCID 20716712, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

5 g (22.4 mmol) of 6-bromo-2-naphthol, 6 ml (67.2 mmol) of methyl acrylate, 100 mg (0.45 mmol) of palladium acetate and 25 ml of triethylamine were placed in a flask gassed with nitrogen. After the addition of 545 mg (1.79 mmol) of tri-(o-tolyl)-phosphine the reaction mixture was boiled under reflux overnight. After 15 hours the reaction was interrupted and the mixture was partitioned between ethyl acetate and water. The organic phase was back-washed three times with water and the aqueous phases were each individually back-washed twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered over Celite and evaporated completely in a vacuum. Chromatography on silica gel with toluene/ethyl acetate (3:2) and subsequent recrystallization from ethyl acetate gave 3.65 g of methyl (E)-3-(6-hydroxy-naphthalen-2-yl)-acrylate. ##STR35##

Workup

  1. temperatureunder reflux overnight
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was back-washed three times with water
  4. washeach individually back-washed twice with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered over Celite
  7. customevaporated completely in a vacuum
  8. customChromatography on silica gel with toluene/ethyl acetate (3:2) and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-7761ef8c04374894856a5dd1b6038be7
Source dataset
uspto-grants-2000_08
Patent number
US06107427

Reaction notes

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