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

HRID 1811616Notes

Reaction equation

HRID 1811616 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-974dfb562a224a2d90f89b313854abdd
Source dataset
uspto-grants-2013_01
Patent number
US08362305B2

Reaction notes

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