2,4,6-Trimethoxybenzaldehyde → 4-(3-(2,4,6-Trimethoxyphenyl)propyl)benzene-1,3-diol

HRID 508387Notes

Reaction equation

HRID 508387 reaction equation
COC1C=C(C[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[OH:21])C=C(OC)C=1.[CH3:22][O:23][C:24]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[C:25]=1[CH:26]=O>>[CH3:22][O:23][C:24]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[C:25]=1[CH2:26][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[OH:21]

Participants

3

Reactant 2

HCID 700192,4,6-TrimethoxybenzaldehydeHCID 446117114-(3-(3,5-Dimethoxyphenyl)propyl)benzene-1,3-diol

Product 1

HCID 446118434-(3-(2,4,6-Trimethoxyphenyl)propyl)benzene-1,3-diol

Procedure

Compound 31 was synthesized following a similar procedure as described for compound 28 above using as starting materials 2,4-dibenzyloxyacetophenone and 2,4,6-trimethoxybenzaldehyde. 1H-NMR (MeOD, 500 MHz): δ 6.822 (d, 1H, J=8.0 Hz), 6.250(d, 1H, J=2.5 Hz), 6.197(dd, 1H, J=2.5 & 8.0 Hz), 6.165(s, 2H), 3.768(s, 3H), 3.764(s, 6H), 2.562(t, 2H, J=7.5 Hz), 2.461(t, 2H, J=7.5 Hz), 1.617-1.653(m, 2H). 13C-NMR (MeOD, 125 MHz): δ 159.273(C), 158.729(2C), 155.556(C), 155.449(C), 129.655 (2CH), 120.426(C), 111.382(C), 105.789(CH), 101.968(CH), 90.285(CH), 54.655 (2CH3), 54.274(CH3), 29.716(CH2), 29.064(CH2), 22.142(CH2).

Sources & evidence

ORD record
ord-0174552eb35a484aa49cf829d9332a2e
Source dataset
uspto-grants-2015_08
Patent number
US09096507B2

Reaction notes

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