Decanal → HCID 14403850, compound

HRID 1194138Notes

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:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>>[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]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[OH:30])[O:13][CH2:14]1

Participants

Reactant 2

HCID 8175Decanal

HCID 14403835HCID 14403835, compound

Product 1

HCID 14403850HCID 14403850, compoundYield 38%

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 n-decanal to obtain (E)-2-[2-(5,5-dimethyl-1,3-dioxan-2-yl)ethenyl]3,5-dimethyl-α-nonylbenzenemethanol as a white solid (955.4 mg, 38%): 59°-61° C.; IR (KBr) 3320, 2900, 2820, 1460 and 1375 cm-1 ; NMR (DMSO-d6) δ 0.72 (3H, s), 0.86 (3H, t, J=8 Hz), 1.14 (3H, s), 1.22 (14H, broad singlet), 1.40-1.56 (2H, m), 2.18 (3H, s), 2.26 (3H, s), 3.54 (2H, d, J=12 Hz), 3.64 (2H, d, J=12 Hz), 4.66-4.76 (1H, m), 4.90 (1H, d, J=5 Hz, exchangeable), 5.06 (1H, d, J=6 Hz), 5.58 (1H, dd, J=5, 15 Hz), 6.72 (1H, d, J=15 Hz), 6.92 (1H, s), 7.18 (1H, s).

Sources & evidence

ORD record: ord-74ae7508e32a4d57a2009a3b8cb5f58f
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812583

Reaction notes

Loading…