HCID 178516607, compound → HCID 9882004, compound

HRID 393869Notes

Reaction equation

HRID 393869 reaction equation
[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2>C1C=CC=CC=1.[Ag]>[OH:1][CH2:2][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:13])[C:2](=[O:1])[CH:11]=1

Participants

4

Reactant 1

HCID 178516607HCID 178516607, compound

Product 1

HCID 9882004HCID 9882004, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 6-bromohexanol-1 (4.5 g, 24.85 mmol) and the silver salt of 2-hydroxy-1,4-naphthoquinone (6.46 g, 23.01 mmol) in benzene (24 mL) was stirred for 48 h at 60° C. The reaction mixture was worked up as described for 2 and crystallized from hexane to afford a yellow solid (3.18 g, 50%). mp 96-98° C., 1H NMR (CDCl3) 8.12 (d, J=7.5 Hz, 1H), 7.87 (d, J=7.7 Hz, 1H), 7.70 (t, J=7.5 Hz, 1H), 7.58 (t, J=7.5 Hz, 1H), 5.95 (s, 1H), 4.15 (t, J=6.3 Hz, 2H), 3.69 (t, J=6.2 Hz, 2H), 1.92-1.97 (m, 2H), 1.3-1.8 (m, 7H)

Workup

  1. customcrystallized from hexane

Sources & evidence

ORD record
ord-ab239803b3074be480d55f0a3663b9aa
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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