Water → 7-Benzyloxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

HRID 1282245Notes

Reaction equation

HRID 1282245 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[CH2:15]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3168407-Hydroxy-6-methoxy-1-tetralone

Product 1

HCID 218627167-Benzyloxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-oneYield 62.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.5 g (0.0233 mole) of 7-hydroxy-6-methoxy-1-tetralone, 5.4 g (0.032 mole) of benzyl bromide and 10 g (0.072 mole) of K2CO3 in 150 ml of acetone was heated to reflux overnight. The reaction as cooled, poured into water and extracted with EtOAc. The EtOAc was dried over Na2SO4 and evaporated to give 7 g of crude product. Crystallization with Et2O gave 4.13 g of product as a white solid, mp 110-111° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe reaction
  4. temperatureas cooled
  5. extractionextracted with EtOAc
  6. dry with materialThe EtOAc was dried over Na2SO4
  7. customevaporated
  8. customto give 7 g of crude product
  9. customCrystallization with Et2O

Sources & evidence

ORD record
ord-33151e0b0c7f4f529582ec4a79c81cd7
Source dataset
uspto-grants-2002_09
Patent number
US06455572B1

Reaction notes

Loading…