4-Hydroxybenzaldehyde → HCID 86600745, compound

HRID 2422917Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH-].[CH2:11]([N+:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O-:1])=[CH:3][CH:4]=1)=[O:7].[CH2:24]([N+:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A glass flask with reflux condenser, heatable oil bath, mechanical stirrer and internal thermometer was charged at room temperature with 7.64 g of 4-hydroxybenzaldehyde and 93.86 g of water and these components were stirred together thoroughly. Subsequently 40.54 g of tetrabutylammonium hydroxide (40% strength in MeOH) were added and the reaction mixture was heated to 60° C. It was stirred at 60° C. for one hour (the contents of the flask became clear). Then the reaction mixture was cooled and the solvents (methanol and water) were distilled off under reduced pressure, 20 mbar, at 30-45° C. The product was then washed with butyl acetate and dried at 80° C. and 10 mbar in a vacuum drying cabinet. This gave a white-beige solid.

Workup

temperatureA glass flask with reflux condenser, heatable oil bath, mechanical stirrer
stirringIt was stirred at 60° C. for one hour (the contents of the flask
temperatureThen the reaction mixture was cooled
distillationthe solvents (methanol and water) were distilled off under reduced pressure, 20 mbar, at 30-45° C
washThe product was then washed with butyl acetate
customdried at 80° C.
custom10 mbar in a vacuum drying cabinet
customThis gave a white-beige solid

Sources & evidence

ORD record: ord-e7613f21d6b4408db05e3d42562d3c9b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960446B2

Reaction notes

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