Benzaldehyde → HCID 14403851, compound

HRID 1194140Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[CH:12]1[O:17][CH2:16][C:15]([CH3:19])([CH3:18])[CH2:14][O:13]1.[CH:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:18][C:15]1([CH3:19])[CH2:16][O:17][CH:12](/[CH:11]=[CH:10]/[C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:27])[O:13][CH2:14]1

Participants

Reactant 2

HCID 240Benzaldehyde

HCID 14403835HCID 14403835, compound

Product 1

HCID 14403851HCID 14403851, compoundYield 81%

Procedure

In the manner described in Example 1, (E)-2-[2-(2-bromo-4,6-dimethylphenyl)ethenyl]-5,5-dimethyl-1,3-dioxane was reacted with benzaldehyde to obtain (E)-2-[2-(5,5-dimethyl-1,3-dioxan-2-yl)ethenyl]3,5-dimethyl-α-phenylbenzenemethanol as a clear foam (271 mg, 81%): IR (film) 3420, 2940, 2840, 1660 and 1605 cm-1 ; NMR (DMSO-d6) δ 0.72 (3H, s), 1.14 (3H, s), 2.20 (3H, s), 2.24 (3H, s), 3.56 (2H, d, J=12 Hz), 3.64 (2H, d, J=12 Hz), 5.08 (1H, d, J=5 Hz), 5.64 (1H, dd, J=5, 15 Hz), 5.74 (1H, d, J=3 Hz, exchangeable), 5.90 (1H, d, J=3 Hz), 6.76 (1H, d, J=15 Hz), 6.96 (1H, s), 7.14 (1H, s), 7.16-7.36 (5H, m).

Sources & evidence

ORD record: ord-9496258c697e47cea53849cc3056d3fb
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812583

Reaction notes

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