Hydrochloric Acid → 4-(2-Methyl-benzylsulfanyl)-benzaldehyde

HRID 1160291Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([CH3:18])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][SH:17].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.O>[CH3:18][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][S:17][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4-fluoro-benzaldehyde (1.16 g, 9.32 mmol) was added dropwise over 2 minutes to a solution of o-tolyl-methanethiol (1.35 g, 9.79 mmol) and Cesium carbonate (3.19 g, 9.79 mmol) in DMF (20 mL). The solution was stirred at 40° C. overnight and then poured into copious water. The pH of the solution was adjusted to 4 with 1N HCl(aq), and the aqueous solution was extracted with ethyl acetate (2×35 mL). The combined organic layers were washed with water, followed by brine. The combined organic layers were then dried (Na2SO4) and the solvent removed under reduced pressure. The resulting residue was purified via radial chromatography (15% ethyl acetate in hexanes) to yield 1.29 g (54%) of 4-(2-Methyl-benzylsulfanyl)-benzaldehyde (28.1). LC/MSD m/e: 243.0 (M+H).

Workup

extractionthe aqueous solution was extracted with ethyl acetate (2×35 mL)
washThe combined organic layers were washed with water
dry with materialThe combined organic layers were then dried (Na2SO4)
customthe solvent removed under reduced pressure
customThe resulting residue was purified via radial chromatography (15% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-4e4fbc0897604a6b816d4a940dd85f50
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816367B2

Reaction notes

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