Benzyl Bromide → 6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

HRID 1771476Notes

Reaction equation

HRID 1771476 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CN(C=O)C.O>[CH2:25]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2)[C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 106822416-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-oneYield 69.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 6-hydroxy-1-tetralone (50.0 g, 308 mmol), K2CO3 (64.0 g, 434 mmol) and BnBr (58.0 g, 340 mmol) in DMF (400 mL) was stirred at 25° C. for 16 hours. The mixture was diluted in water (1000 mL), extracted with EtOAc (1000 mL×3). The combined organic layers were washed with brine (500 mL×3), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the product as a brown solid (54.0 g, yield 69%).

Workup

  1. extractionextracted with EtOAc (1000 mL×3)
  2. washThe combined organic layers were washed with brine (500 mL×3)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3d73289995e454e9932e1730e20dfe4
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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