Reaction #943989

ord-2be790c6a8a041b4bc60d9a2b9a17b3d

Reaction equation

O
water
COc1cc2c(cc1O)C(=O)CCC2
7-hydroxy-6-methoxy-1-tetralone
BrCc1ccccc1
benzyl bromide
O=C([O-])[O-].[K+].[K+]
K2CO3
→
COc1cc2c(cc1OCc1ccccc1)C(=O)CCC2
product
Yield 62.8%
COc1cc2c(cc1OCc1ccccc1)C(=O)CCC2
7-Benzyloxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
Yield 62.8%

Reactants

O
water
COc1cc2c(cc1O)C(=O)CCC2
7-hydroxy-6-methoxy-1-tetralone
BrCc1ccccc1
benzyl bromide
O=C([O-])[O-].[K+].[K+]
K2CO3

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas heated
  2. 2
    Temperatureto reflux overnight
  3. 3
    OtherThe reaction
  4. 4
    Temperatureas cooled
  5. 5
    Extractionextracted with EtOAc
  6. 6
    DryingThe EtOAc was dried over Na2SO4
  7. 7
    Otherevaporated
  8. 8
    Otherto give 7 g of crude product
  9. 9
    OtherCrystallization with Et2O

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE039419E1uspto-grants-2006_12