1,6-Diiodohexane → 1,2-Dihydro-4-(6-iodohexyloxy)-1,2-dioxonaphthalene

HRID 852815

Reaction equation

HRID 852815 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][I:8].[OH:9][C:10]1[C:11](=[O:21])[C:12]2[C:17]([C:18](=[O:20])[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2>C1C=CC=CC=1.[Ag]>[I:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:20][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:21])[C:10](=[O:9])[CH:19]=1

Participants

5

Reactant 2

HCID 123731,6-DiiodohexaneHCID 178516607HCID 178516607, compound

Product 1

HCID 226477941,2-Dihydro-4-(6-iodohexyloxy)-1,2-dioxonaphthaleneYield 57%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 1,6-diiodohexane (10.14 g, 30 mmol) and the silver salt of 2-hydroxy-1,4-naphthoquinone (2.81 g, 10 mmol) in benzene (60 mL) was stirred for 12 h at room temperature. The reaction mixture was filtered through Celite, concentrated in vacuo, and purified by flash chromatography (hexane/EtOAc 4:1) to give a yellow solid (2,19 g, 57%); mp 85-87° C.; 1H NMR (CDCl3) 8.12 (dd, J=6.5, 1.0 Hz, 1H), 7.86 (dd, J=6.9, 0.9 Hz, 1H), 7.70 (dt, J=7.6, 1.5 Hz, 1H), 7.58 (dt, J=7.5, 1.3 Hz, 1H), 5.95 (s, 1H), 4.15 (t, J=6.3, 2H), 3.22 (t, J=6.9 Hz, 2H), 1.80-2.05 (m, 4H), 1.45-2.10 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-708a7b2daea54f11b6d9f119486b89a4
Source dataset
uspto-grants-2007_08
Patent number
US07253207B2

Linked notes

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