4-Hydroxybenzaldehyde → 3-(1-Admantyl)-4-hydroxybenzaldehyde

HRID 717677Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14](O)=[CH:13][CH:12]=1>>[C:11]12([C:3]3[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=3[OH:1])[CH:6]=[O:7])[CH2:16][CH:15]3[CH2:4][CH:5]([CH2:8][CH:13]([CH2:14]3)[CH2:12]1)[CH2:6]2

Participants

Reactant 2

HCID 1264-Hydroxybenzaldehyde

HCID 78084-Bromophenol

Product 1

HCID 34078923-(1-Admantyl)-4-hydroxybenzaldehydeYield 56%

Procedure

When 4-hydroxybenzaldehyde was substituted for 4-bromophenol in Example 31, Step A, the similar procedure afforded 3-(1-admantanyl)-4-hydroxybenzaldehyde in 56% yield, as a pale white solid. 1H-NMR (CDCl3) 9.84 (s, 1H); 7.78 (d, 1H, J=2.07 Hz); 7.61 (dd, 1H, J=8.13, 2.01 Hz); 6.77 (d, 1H, J=8.16 Hz); 5.88 (bs, 1H); 2.12 (s, 6H); 2.09 (s, 3H); 1.78 (s, 6H). This was methylated by similar procedure as described in Example 31, Step B, to give the title compound in 64% yield, as light yellow solid. 1H-NMR (CDCl3) 9.86 (s, 1H); 7.76 (d, 1H, J=2.07 Hz); 7.7 (dd, 1H, J=8.4, 2.1 Hz); 6.95 (d, 1H, J=8.4 Hz); 3.91 (s, 3H); 2.09 (s, 9H); 1.76 (s, 6H).

Sources & evidence

ORD record: ord-1f0c4c56ead64ea38780a9d3149cbe71
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

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