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

HRID 1811615Notes

Reaction equation

HRID 1811615 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-2ba88945a4994d4398f21cdf719a8bab
Source dataset
uspto-grants-2013_01
Patent number
US08362305B2

Reaction notes

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