Water → 2-Benzyloxy-4-dibutylaminobenzaldehyde

HRID 85242Notes

Reaction equation

[CH2:1]([N:5]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([OH:14])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O.C(OCC)(=O)C>[CH2:19]([O:14][C:8]1[CH:7]=[C:6]([N:5]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:1][CH2:2][CH2:3][CH3:4])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In 20 ml of 1-methyl-2-pyrrolidone were dissolved 1.86 g (7.46 mmol) of 4-dibutylamino-2-hydroxybenzaldehyde and 1.66 g (9.71 mmol) of benzyl bromide. To this mixture was added 2.06 g (14.9 mmol) of anhydrous potassium carbonate and the mixture was stirred with heating at 50° C. for 2 hours. After the reaction mixture was added to water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 2.31 g of a pale yellow crystal (yield: 91.3%).

Workup

washwashing with a saturated saline solution
dry with materialdrying over anhydrous sodium sulfate, and concentration
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-e8311cb2e9514591ae7744cdf976ba70
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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