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

HRID 856807

Reaction equation

HRID 856807 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-2be790c6a8a041b4bc60d9a2b9a17b3d
Source dataset
uspto-grants-2006_12
Patent number
USRE039419E1

Linked notes

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