3-(1-Admantyl)-4-hydroxybenzaldehyde → Methyl 4-(1-admantyl)-3-isopropoxybenzoate

HRID 710455Notes

Reaction equation

HRID 710455 reaction equation
[C:1]12([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=3[OH:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:22]12(C3C=C(C=CC=3O)C=O)CC3CC(CC(C3)[CH2:23]1)[CH2:29]2>>[C:1]12([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=3[O:21][CH:22]([CH3:29])[CH3:23])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

3

Reactant 2

HCID 34078923-(1-Admantyl)-4-hydroxybenzaldehydeHCID 19387991Methyl 3-hydroxy-4-(1-adamantyl)benzoate

Product 1

HCID 66729638Methyl 4-(1-admantyl)-3-isopropoxybenzoateYield 75.4%

Procedure

When methyl 4-(1-admantyl)-3-hydroxybenzoate was substituted for 3-(1-admantyl)-4-hydroxybenzaldehyde in Example 60, Step A, the identical process afforded the title compound (0.95 g, 75.4%) as a colourless solid. 1H-NMR (CDCl3) 1.39 (d, 6H, J=6 Hz); 1.75 (5, 6H); 2.05 (s, 3H); 2.11 (s, 6H); 3.87 (s, 3H); 4.69-4.71 (m, 1H); 7.24 (d, 1H, J=8.1 Hz); 7.47 (b, 1H); 7.51 (dd, 1H, J=1.55, 8.09 Hz).

Sources & evidence

ORD record
ord-bc24a65393ea4ad7b135cd17e0e86884
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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