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

HRID 245590

Reaction equation

HRID 245590 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-d957cedbb1854089aefea1c7ab67ccc6
Source dataset
uspto-grants-2014_02
Patent number
US08658838B2

Linked notes

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