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

HRID 1170960Notes

Reaction equation

HRID 1170960 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[CH:5]=O.Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:14]=1.C(O)(C(F)(F)F)=O.O>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:5][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:14]=2)[CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 22392675Trifluoroacetic acid waterHCID 66642860HCID 66642860, compound

Product 1

HCID 66642786HCID 66642786, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-73751454b9f541e99670e34d6f64d441
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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