Reacción #943989

ord-2be790c6a8a041b4bc60d9a2b9a17b3d

Ecuación de reacción

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
Rendimiento 62.8%
COc1cc2c(cc1OCc1ccccc1)C(=O)CCC2
7-Benzyloxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
Rendimiento 62.8%

Reactantes

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

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas heated
  2. 2
    Temperaturato reflux overnight
  3. 3
    OtroThe reaction
  4. 4
    Temperaturaas cooled
  5. 5
    Extracciónextracted with EtOAc
  6. 6
    SecadoThe EtOAc was dried over Na2SO4
  7. 7
    Otroevaporated
  8. 8
    Otroto give 7 g of crude product
  9. 9
    OtroCrystallization with Et2O

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE039419E1uspto-grants-2006_12