M-Cresol → 3-(3-Methylphenoxy)benzaldehyde

HRID 2422252Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17].C(=O)([O-])[O-].[K+].[K+].N1C2C(=CC=CC=2)C=CC=1>[Cu]=O.N1C=CC=CC=1>[CH3:17][C:11]1[CH:10]=[C:15]([CH:14]=[CH:13][CH:12]=1)[O:16][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 3-bromobenzaldehyde (7.01 g, 37.9 mmol), m-cresol (4.51 g, 41.7 mmol), copper oxide (II) (4.53 g, 56.9 mmol), potassium carbonate (7.86 g, 56.9 mmol), pyridine (50 mL) and quinoline (25 mL) was stirred under a nitrogen atmosphere at 170° C. for 24 hrs. The reaction mixture was cooled and pyridine was evaporated under reduced pressure. Ethyl acetate was added to the residue, the insoluble material was filtered off, and the filtrate was washed with 1 M hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane-10% ethyl acetate/hexane) to give the title compound (5.80 g, 72%) as a pale-brown oil.

Workup

temperatureThe reaction mixture was cooled
custompyridine was evaporated under reduced pressure
additionEthyl acetate was added to the residue
filtrationthe insoluble material was filtered off
washthe filtrate was washed with 1 M hydrochloric acid and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane-10% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-83e5591d14fe4cd6aa276420a9bd8bc1
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960369B2

Reaction notes

Loading…