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

HRID 2108599Notes

Reaction equation

HRID 2108599 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-propyl-benzyl)phenol was prepared from 3,5-dimethyl-4-hydroxy benzaldehyde and bromo-4-methoxymethoxy-3-iso-propylbenzene according to the procedure described in Chiellini et al., Bioorg. Med. Chem. Lett. 10:2607 (2000) 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, 1H), 6.83 (s, 2H), 6.77 (d, J=7.5 Hz, 1H), 6.65 (d, J=7.5 Hz, 1H), 4.0 (d, J=9.9 Hz, 2H), 3.75(s, 2H), 3.20-3.29 (m, 1H), 2.28 (s, 6H), 1.19 (d, J=6.6 Hz, 6H); 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-7e15d77f44e543bc9d6290c7b88171ee
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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