Formaldehyde → 3-Hydroxy-5-methoxybenzaldehyde

HRID 591852Notes

Reaction equation

C([S-])C.[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15]C)[CH:14]=1)[CH:10]=[O:11].[Cl-].[Na+].C=O>CN(C=O)C.C(O)(=O)C>[OH:15][C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([O:6][CH3:5])[CH:14]=1)[CH:10]=[O:11]

Participants

Conditions

Temperature: 145 °C

Procedure

To a 1.0-L three-neck flask was added sodium ethanethiolate (80%, 28.5 g, 271.0 mmol) and anhydrous DMF (225 mL). The mixture was heated to 145° C. for 1.5 hours. Then, 3,5-dimethoxy-benzaldehyde (15.0 g, 90.0 mmol) in anhydrous DMF (350 mL) was added over a period of 8 minutes. The reaction was kept at 145° C. for another 1 hour, then cooled to room temperature. Saturated sodium chloride solution (2.5 L) and formaline (37%, 240 mL) together with acetic acid (500 mL) was added. The resulting solution was thoroughly extracted with ethyl acetate, the organic phase was dried with sodium sulfate, and the solvent was removed under vacuum. The crude compound was purified by column chromatography (silica gel 230-400 mesh; eluting with dichloromethane and ethyl acetate 7:1) to give 3-hydroxy-5-methoxy-benzaldehyde as a white solid. Yield: 12.0 g (88%).

Workup

temperaturecooled to room temperature
extractionThe resulting solution was thoroughly extracted with ethyl acetate
dry with materialthe organic phase was dried with sodium sulfate
customthe solvent was removed under vacuum
customThe crude compound was purified by column chromatography (silica gel 230-400 mesh; eluting with dichloromethane and ethyl acetate 7:1)

Sources & evidence

ORD record: ord-6b83a0545af844a8a105b420cf9ba709
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238640B2

Reaction notes

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