(4-(1-Admantyl)-3-isopropoxyphenyl)methanol → 4-(1-Admantyl)-3-isopropoxybenzaldehyde

HRID 710457Notes

Reaction equation

HRID 710457 reaction equation
[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]=3[O:19][CH:20]([CH3:22])[CH3:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>O1CCOCC1.O=[Mn]=O>[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:12]=3[O:19][CH:20]([CH3:22])[CH3:21])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 1

HCID 66726726(4-(1-Admantyl)-3-isopropoxyphenyl)methanol

Product 1

HCID 871264764-(1-Admantyl)-3-isopropoxybenzaldehydeYield 73.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of Step B (0.7 g) and MnO2 (1.5 g) in dioxane (20 ml) was stirred for 6 h at reflux. The mixture was filtered through Celite pad and the filtrate was evaporated to dryness to give the title compound (0.51 g, 73.4%) as creamy solid. 1H-NMR (CDCl3) 1.4 (d, 6H, J=6 Hz); 1.76 (s, 6H); 2.07 (s, 3H); 2.11 (s, 6H); 4.7-4.78 (m, 1H); 7.32-7.42 (m, 3H); 9.91 (s, 1H).

Workup

  1. temperatureat reflux
  2. filtrationThe mixture was filtered through Celite pad
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-d13e7fe184c24c3c998fd1502af85479
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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