Hydrogen Bromide → 1-(6-Hydroxy-2-naphthalenyl)-1-propanone

HRID 1734126Notes

Reaction equation

HRID 1734126 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13](=[O:16])[CH2:14][CH3:15])[CH:9]=2)[CH:4]=1.Br>C(O)(=O)C>[C:13]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]2)(=[O:16])[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 759131-(6-Methoxy-2-naphthalenyl)-1-propanone

Product 1

HCID 214748621-(6-Hydroxy-2-naphthalenyl)-1-propanoneYield 56.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 10 g of 2-methoxy-6-propionyl-naphthalene, prepared according to J. Chem. Soc. (1934), p. 864, in acetic acid (45 ml) and kept under reflux, 47 ml of aqueous HBr (48% by weight) is added during a three-hour time period. The resulting suspension is poured onto 500 g of crushed ice; the formed tars are left in the reaction flask. A suspension is obtained which is filtered on a Buchner filter. The solid material is washed with 100 ml of water, 50 ml of saturated aqueous solution of NaHCO3, and then with 50 ml of water. After drying in air and in an oven at 60° C. for 10 hours, 5.3 g of pink-white product is obtained with the following characteristics:

Workup

  1. temperatureunder reflux
  2. waitthe formed tars are left in the reaction flask
  3. customA suspension is obtained which
  4. filtrationis filtered on a Buchner
  5. filtrationfilter
  6. washThe solid material is washed with 100 ml of water, 50 ml of saturated aqueous solution of NaHCO3
  7. customAfter drying in air and in an oven at 60° C. for 10 hours

Sources & evidence

ORD record
ord-4ab91880185e47a6add8051b79bc8c6f
Source dataset
uspto-grants-1996_07
Patent number
US05532361

Reaction notes

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