Water → 4-Methoxy-3-[6-(4-phenylbut-1-yloxy)hex-1-yloxy]benzaldehyde

HRID 377626Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C)C=O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 3-hydroxy-4-methoxybenzaldehyde (4.8 grams) in dimethylformamide (100 ml) at room temperature is added potassium carbonate (4.9 grams) and 1-bromo-6-(4-phenylbut-1-yloxy)hexane (10.0 grams). After stirring at 80° C. over 4 hours the reaction mixture is poured into water and extracted with ethyl acetate. The combined organics are washed with 1N sodium hydroxide and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting amber oil is filtered through a 5×10 cm pad of silica gel, eluting with a 1:3 mixture of ethyl acetate and hexane, to give 12.0 grams of a colorless oil. MS (m/z) 384.

Workup

extractionextracted with ethyl acetate
washThe combined organics are washed with 1N sodium hydroxide and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationThe resulting amber oil is filtered through a 5×10 cm pad of silica gel
washeluting with a 1:3 mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-d9a5e50754914e5992451769dfb68347
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028086

Reaction notes

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