3,5-Dimethyl-4-hydroxybenzaldehyde → HCID 66642786, compound

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Reaction Steps

Intermediate 2,6-dimethyl-4-(4′-methoxymethoxy-3′-iso-propylbenzyl)phenol was prepared from 3,5-dimethyl-4-hydroxy benzaldehyde and bromo-4-methoxymethoxy-3-iso-propylbenzene according to the procedure described in G. Chiellini et al. Biorg. Med. Chem. Lett. 2000, 10, 2607 and transformed into the title compound according to the procedure described for the synthesis of compound 7-17, step b; (0.12 g, 85%); 1H NMR (300 MHz, CD3OD): δ 6.97 (s, 1 H), 6.83 (s, 2 H), 6.77 (d, J=7.5 Hz, 1 H), 6.65 (d, J=7.5 Hz, 1 H), 4.0 (d, J=9.9 Hz, 2 H), 3.75 (s, 2 H), 3.20-3.29 (m, 1 H), 2.28 (s, 6 H), 1.19 (d, J=6.6 Hz, 6 H); LC-MS m/z=363 [C20H25O6P−H]+; (94%) HPLC conditions: ODSAQ AQ-303-5 column; mobile phase=CH3OH: 0.05% TFA/H2O (7:3) flow rate=1.0 mL/min; detection=UV@254 nm retention time in min: 10.92; Anal Calcd for (C20H25O6P+1.2H2O): C, 59.12; H, 7.15. Found: C, 58.96; H, 6.77.

Provenance & Evidence