1-(6-Methoxy-2-naphthyl)heptan-1-ol → 1-(6-Methoxynaphthalen-2-yl)heptan-1-one

HRID 898287

Reaction equation

HRID 898287 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([OH:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:7]=[CH:6]2.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 223273441-(6-Methoxy-2-naphthyl)heptan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 100617011-(6-Methoxynaphthalen-2-yl)heptan-1-oneYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the 1-(6-methoxy-2-naphthyl)heptan-1-ol (101.1 g, 371 mmol) in CH2Cl2 (1000 mL) under N2 was added pyridinium chlorochromate (120.02 g, 556.74 mmol). The reaction was stirred for a total of 3 h and then poured onto an alumina column (2000 g, basic Brockman activity, 60-325 mesh). Column was eluted with CH2Cl2. Product was collected, filtered, rotovap'd and dried in vacuo to give the product as a white solid (81.5 g, 301.44 mmol, 81%) with mp 69-72° C. 177 mg of crude ketone was recrystallized from methanol to give the desired product as a white solid (105 mg) mp 70-72° C.; 1H NMR (DMSO-d6) δ 0.86 (m, 3H), 1.25-1.40 (m, 6H), 1.60-1.70 (m, 2H), 3.07 (t, J=7.3 Hz, 2H), 3.90 (s, 3H), 7.24 (d, J=9 Hz, 1H), 7.39 (s, 1H), 7.87 (d, J=8.7 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 8.02 (d, J=8.9, 1H) 8.58 (s, 1H); IR (solid) 2910, 2870, 1660, 1630, 1470, and 1180 cm−1; mass spectrum [EI], m/z 271 (M+H)+;

Workup

  1. additionpoured onto an alumina column (2000 g, basic Brockman activity, 60-325 mesh)
  2. washColumn was eluted with CH2Cl2
  3. customProduct was collected
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2512e4c1aa794e739d008bba442e1ea9
Source dataset
uspto-grants-2008_04
Patent number
US07351730B2

Linked notes

Loading…