2,4-Dihydroxybenzaldehyde → HCID 10537643, compound

HRID 322948Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:14][C:15]1[CH:19]=[CH:18][S:17][CH:16]=1>CN(C)C=O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2,4-dihydroxybenzaldehyde (42.6 g) in dimethylformamide (250 mL) at ambient temperature is treated with sodium hydride (13.5 g; 60% w/v dispersion in mineral oil; 338 mmol), portionwise during 30 minutes. It is then treated with 3-chloromethylthiophene and the reaction mixture is heated at 60° C. for 3 hours. The mixture is concentrated in vacuo and the residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL) and the combined organic extracts are washed with brine (50 mL), dried over magnesium sulphate, filtered and the solvent is removed in vacuo. Flash chromatography on silica gel, using a mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent, gives 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (11.8 g), in the form of a white solid.

Workup

concentrationThe mixture is concentrated in vacuo
customthe residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL)
extractionThe aqueous layer is extracted with ethyl acetate (3×100 mL)
washthe combined organic extracts are washed with brine (50 mL)
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent is removed in vacuo
additiona mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent

Sources & evidence

ORD record: ord-c8c18f4c75874b1a910d5d856be4a462
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211234B1

Reaction notes

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