(E)-2-(1-Admantyl)-1-isopropoxy-4-(2-nitrovinyl)benzene → (4-(1-Admantyl)-3-isopropoxyphenyl)methanol

HRID 710456Notes

Reaction equation

HRID 710456 reaction equation
[C:1]12([C:11]3[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][C:12]=3[O:21][CH:22]([CH3:24])[CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12(C3C=C(/C=C/[N+]([O-])=O)C=CC=3OC(C)C)CC3CC(CC(C3)C1)C2>>[C:1]12([C:11]3[CH:20]=[CH:19][C:14]([CH2:15][OH:16])=[CH:13][C:12]=3[O:21][CH:22]([CH3:24])[CH3:23])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

3

Reactant 2

HCID 66727011(E)-2-(1-Admantyl)-1-isopropoxy-4-(2-nitrovinyl)benzeneHCID 66729638Methyl 4-(1-admantyl)-3-isopropoxybenzoate

Product 1

HCID 66726726(4-(1-Admantyl)-3-isopropoxyphenyl)methanolYield 89%

Procedure

When the product of Step A was substituted for (E)-2-(1-Admantyl)-1-isopropoxy-4-(2-nitrovinyl)benzene in Example 60, Step C, the identical process afforded the title compound in 89% yield, as creamy paste. 1H-NMR (CDCl3) 1.38 (d, 6H, J=6 Hz); 1.75 (s, 6H); 2.04 (s, 3H); 2.1 (s, 6H); 4.62 (s, 2H); 4.53-4.71 (m, 1H); 6.79-6.9 (m, 2H); 7.20 (d, 1H, J=7.88 Hz).

Sources & evidence

ORD record
ord-72f940c385b44f98ac07057137bb2630
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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