2-Isopropylphenol → HCID 57457861, compound

HRID 1821669Notes

Reaction equation

[H-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([CH3:5])[CH3:4].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18]Cl>O1CCCC1>[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

In dry tetrahydrofuran (60 mL) was suspended 4.80 g (120 mmol) of 60% sodium hydride, and a dry tetrahydrofuran (80 mL) solution containing 13.6 g (100 mmol) of 2-isopropylphenol was added dropwise to the suspension at 0° C. After stirring at 0° C. for 10 minutes, a dry tetrahydrofuran (80 mL) solution containing 14.9 g (119 mmol) of 2-methoxyethoxymethyl chloride was added dropwise thereto. The reaction mixture was stirred in an ice bath for 2 hours, poured into ice-cold water (250 mL), and extracted with ethyl acetate. The organic layers were combined, washed succeccively with 1 mol/L aqueous sodium hydroxide solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=50:1) to obtain 18.1 g (80.8 mmol, Yield: 80.8%) of 1-isopropyl-2-[(2-methoxyethoxy)methoxy]benzene.

Workup

additionwas added dropwise to the suspension at 0° C
additionwas added dropwise
stirringThe reaction mixture was stirred in an ice bath for 2 hours
extractionextracted with ethyl acetate
washwashed succeccively with 1 mol/L aqueous sodium hydroxide solution and brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed
customthe residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=50:1)

Sources & evidence

ORD record: ord-df622c6807794f339e6440aa69b40cd1
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608563B2

Reaction notes

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