Potassium Iodide → Acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester

HRID 1728065

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[C:19]([O:22][CH2:23][CH2:24]Br)(=[O:21])[CH3:20]>CN(C)C=O.C(OCC)C>[CH:4]([C:3]1[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:2]=1[O:1][CH2:24][CH2:23][O:22][C:19](=[O:21])[CH3:20])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-hydroxy-5-methyl-benzaldehyde (2.4 g, 18 mmol) (Aldrich) in N,N-dimethylformamide (30 mL) was added cesium carbonate (6 g, 18 mmol), potassium iodide (3 g, 18 mmol) and 2-bromoethyl acetate (7 g, 42 mmol), Aldrich). The reaction mixture was heated at 100° C. for 3 h. The mixture was cooled to room temperature and diluted with ethyl ether, washed with water, brine, separated, and concentrated. The residue was purified by chromatography (EtOAc:Hexanes=1:6) to give acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester as a yellow oil (Yield 4 g, 100%).

Workup

temperatureThe mixture was cooled to room temperature
washwashed with water, brine
customseparated
concentrationconcentrated
customThe residue was purified by chromatography (EtOAc:Hexanes=1:6)

Sources & evidence

ORD record: ord-8f54c8c7c2104ec28a3e852fba26fa82
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Linked notes

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