Potassium Carbonate → 2-[4-(Methylsulfanyl)phenoxy]benzaldehyde

HRID 1279638Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2-Fluorobenzaldehyde (31.6 mL, 300 mmol) and 4-(methylmercapto)phenol (46.27 g, 330 mmol) were dissolved in DMF (500 mL) and potassium carbonate (62.2 g, 450 mmol) was then added. The mixture was heated at 100° C. for 12 h under a nitrogen atmosphere. After cooling to room temperature the mixture was evaporated to dryness, co-evaporated with toluene and then partitioned between ethyl acetate and water. The organic layer was separated, washed with water, dried (MgSO4) and evaporated to a brown oil of the desired aldehyde material (84.4 g) which was contaminated with ca 15% of starting phenol, but sufficiently pure to use directly in the next stage; δH(CDCI3, 400 MHz) 2.47 (3 H, s), 6.87 (1 H, d), 6.99 (2 H, m), 7.17 (1 H, m), 7.29 (2 H, m), 7.49 (1 H, m), 7.92 (1 H, d), 10.49 (1 H, s). If required the crude mixture can be purified by flash chromatography [SiO2; ethyl acetate/ hexanes (2→10%)] to obtain a pure sample of the desired aldehyde compound.

Workup

temperatureAfter cooling to room temperature the mixture
customwas evaporated to dryness, co-evaporated with toluene
custompartitioned between ethyl acetate and water
customThe organic layer was separated
washwashed with water
dry with materialdried (MgSO4)
customevaporated to a brown oil of the desired aldehyde material (84.4 g) which
customcan be purified by flash chromatography [SiO2; ethyl acetate/ hexanes (2→10%)]

Sources & evidence

ORD record: ord-2d51f6d1c34c41db8e6a136d4bbd387e
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448293B1

Reaction notes

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