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

HRID 508388Notes

Reaction equation

HRID 508388 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-6c8aa05e5b5c49e7bf6506f9b52df4e4
Source dataset
uspto-grants-2015_08
Patent number
US09096507B2

Reaction notes

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