Benzyl Bromide → 5-Benzyloxy-6-methoxy-1-indanone

HRID 2101082Notes

Reaction equation

HRID 2101082 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 147633965-Benzyloxy-6-methoxy-1-indanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 5-Hydroxy-6-methoxy-indan-1-one (2.1 g), K2CO3 (3.3 g), acetone (30 ml) and benzyl bromide was heated to reflux for 5 hours. The mixture was filtered and the filtrate was evaporated to oil. The oil was treated with diethyl ether (50 ml) and the solid was collected to give 5-Benzyloxy-6-methoxy-indan-1-one (3 g). LC-MS: m/e 269 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to oil
  5. additionThe oil was treated with diethyl ether (50 ml)
  6. customthe solid was collected

Sources & evidence

ORD record
ord-49abdba8cfdf48d58e84817987cf00a5
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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