2,4-Dimethoxy-3-methylbenzaldehyde → 4-(3-(2,4-Dihydroxyphenyl)propyl)-2-methylbenzene-1,3-diol

HRID 245591Notes

Reaction equation

HRID 245591 reaction equation
OC1C=C(C[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[OH:19])C=C(O)C=1.C[O:21][C:22]1[C:29]([CH3:30])=[C:28]([O:31]C)[CH:27]=[CH:26][C:23]=1[CH:24]=O>>[OH:19][C:13]1[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]=1[CH2:11][CH2:10][CH2:24][C:23]1[CH:26]=[CH:27][C:28]([OH:31])=[C:29]([CH3:30])[C:22]=1[OH:21]

Participants

3

Reactant 2

HCID 2516932,4-Dimethoxy-3-methylbenzaldehydeHCID 446118374-(3-(3,5-Dihydroxyphenyl)propyl)benzene-1,3-diol

Product 1

HCID 446119684-(3-(2,4-Dihydroxyphenyl)propyl)-2-methylbenzene-1,3-diol

Procedure

Compound 32 was synthesized following a similar procedure as described for compound 30 using as starting materials 2,4-dibenzyloxyacetophenone and 2,4-dimethoxy-3-methylbenzaldehyde. 1H-NMR (MeOD, 500 MHz): δ 6.879 (d, 1H, J=8.5 Hz), 6.747 (d, 1H, J=8.0 Hz), 6.352 (d, 1H, J=1.5 Hz), 6.341 (d, 1H, J=4.0 Hz), 6.285 (dd, 1H, J=8.0 Hz & 2.5 Hz), 2.567 (dd, 4H, J=8.0 & 7.5 Hz), 2.133 (s, 3H), 1.786-1.817 (m, 2H). 13C-NMR (MeOD, 125 MHz): δ 155.486 (C), 155.316 (C), 153.428 (C), 152.906 (C), 130.295 (CH), 126.523 (CH), 120.933 (C), 120.518 (C), 111.556 (C), 106.788 (CH), 106.377 (CH), 102.283 (CH), 30.767 (CH2), 29.649 (CH2), 29.127 (CH2), 7.833 (CH3).

Sources & evidence

ORD record
ord-227b3e6b6ddc4de2a99f8d238e105295
Source dataset
uspto-grants-2014_02
Patent number
US08658838B2

Reaction notes

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