2-Ethyl-6-methylphenol → HCID 178458381, compound
Reaction equation
[CH2:1]([C:3]1C=C(C=C(C)C=1O)C=O)[CH3:2].C(C1C=CC=C(C)C=1O)C.[CH2:23]([C:25]1[CH:26]=[C:27]([CH:32]=[C:33]([CH3:36])[C:34]=1[OH:35])[C:28]([NH:30][OH:31])=[NH:29])[CH3:24]>>[CH2:3]([O:35][C:34]1[C:33]([CH3:36])=[CH:32][C:27]([C:28]([NH:30][OH:31])=[NH:29])=[CH:26][C:25]=1[CH2:23][CH3:24])[CH:1]=[CH2:2]Participants
4
Procedure
The title compound is prepared by allylating 3-ethyl-4-hydroxy-5-methyl-benzaldehyde which is prepared from 2-ethyl-6-methyl-phenol following literature procedures (see 3-ethyl-4,N-dihydroxy-5-methyl-benzamidine). The aldehyde is then transformed into the corresponding hydroxyamidine according to literature procedures (see 3-ethyl-4,N-dihydroxy-5-methyl-benzamidine); LC-MS: tR=0.72 min, [M+1]+=235.09; 1H NMR (CD3OD): δ 7.31 (s, 1H), 7.29 (s, 1H), 6.10 (m, 1H), 5.43 (dd, J=17.0, 1.5 Hz, 1H), 5.27 (dd, J=10.3, 1.2 Hz, 1H), 4.81 (s br, 3H), 4.31 (d, J=5.6 Hz, 2H), 2.67 (q, J=7.6 Hz, 2H), 2.30 (s, 3H), 1.23 (t, J=7.6 Hz, 4H).
Sources & evidence
- ORD record
- ord-3646e286eba849b9a842024c7ce63e72
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133910B2
Reaction notes
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