1-Bromopentane → (Naphthalen-1-yl)[4-(pentyloxy)naphthalen-1-yl]methanone

HRID 1824728Notes

Reaction equation

HRID 1824728 reaction equation
[C:1]1([C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([OH:23])=[CH:15][CH:14]=2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CC(C)=O>[C:1]1([C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:15][CH:14]=2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 22144261432049-53-1

Product 1

HCID 9799417(Naphthalen-1-yl)[4-(pentyloxy)naphthalen-1-yl]methanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

11.0 g of naphthalen-1-yl-(4-hydroxy-naphthalen-1-yl)-methanone and 6.1 g of potassium carbonate in 130 ml of acetone are stirred for 15 min at reflux. Then, within 2 min, a solution of 6.8 ml 1-bromopentane in 20 ml of acetone is added and the suspension is stirred for additional 22 h at reflux. Conventional workup and subsequent chromatography affords naphthalen-1-yl-(4-pentyloxy-naphthalen-1-yl)-methanone.

Workup

  1. temperatureat reflux
  2. temperatureat reflux

Sources & evidence

ORD record
ord-494e76cb9c214762aa1eaefa1986d4bd
Source dataset
uspto-grants-2006_05
Patent number
US07045533B2

Reaction notes

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