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

HRID 1802128Notes

Reaction equation

HRID 1802128 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.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>>[CH2:13]([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:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 106822416-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-oneYield 80%

Conditions

Temperature
10 °C

Procedure

The mixture of 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (30.74 g, 0.1895 mol), benzyl bromide (27.0 mL, 0.227 mol) and potassium carbonate (39.3 g, 0.284 mol) in acetone (250 mL, 3.4 mol) was heated to reflux under an atmosphere of nitrogen for 3 hours. The mixture was cooled to 10° C. with an ice bath, filtered and washed with small amount of to acetone. The filtrate was concentrated in rotavap. The resulting crystals were collected by filtration and washed with EtOAc-hexane then hexane to give a pale yellow solid product as the first crop. The mother liquid was concentrated in rotavapor and the residue was purified by chromatograph with EtOAc:hexane (0:100 to 20:80) to give the second crop of solid product (38.07 g, 80%). 1H NMR (CHLOROFORM-d) δ: 8.02 (d, J=8.6 Hz, 1H), 7.32-7.51 (m, 5H), 6.91 (dd, J=8.8, 2.3 Hz, 1H), 6.80 (s, 1H), 5.13 (s, 2H), 2.93 (t, J=6.1 Hz, 2H), 2.56-2.68 (m, 2H), 2.12 (quin, J=6.3 Hz, 2H). MS (M+1): 253.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under an atmosphere of nitrogen for 3 hours
  3. filtrationfiltered
  4. washwashed with small amount of to acetone
  5. concentrationThe filtrate was concentrated in rotavap
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with EtOAc-hexane
  8. customhexane to give a pale yellow solid product as the first crop
  9. concentrationThe mother liquid was concentrated in rotavapor
  10. customthe residue was purified by chromatograph with EtOAc:hexane (0:100 to 20:80)

Sources & evidence

ORD record
ord-43263bef13f84b8a98648af893d85330
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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