Ethyl 4-bromobutyrate → 4-(2,3-Dimethoxy-5-formylphenoxy)butanoic acid, ethyl ester

HRID 964432

Reaction equation

HRID 964432 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([OH:13])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].Br[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[CH3:12][O:11][C:10]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[O:13][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

3

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 1415133,4-Dimethoxy-5-hydroxybenzaldehyde

Product 1

HCID 867523784-(2,3-Dimethoxy-5-formylphenoxy)butanoic acid, ethyl ester

Procedure

Employing the method of Preparation 3, 3.30 g (18.41 mmol) of 3,4-dimethoxy-5-hydroxybenzaldehyde is alkylated with ethyl 4-bromobutyrate. 4-(2,3-Dimethoxy-5-formylphenoxy)butanoic acid, ethyl ester is obtained as a yellow-orange oil after drying under high vacuum at 60° C. (5.45 g, 100%): IR (neat) 1735, 1690 cm-1 ; 1 H-NMR (CDCl3) is consistent with the desired product; MS (FAB) m/e 297 (M+ +H). Analysis calculated. for C15H20O6 : C, 60.80; H, 6.80; O, 32.40. Found: C, 60.51; H, 6.86; O, 32.63.

Sources & evidence

ORD record
ord-3e6f10fbea6f4188a376d85ff5531692
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Linked notes

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