Monobenzone → HCID 22397051, compound

HRID 2187599Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[CH3:17]

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 4-(benzyloxy)phenol (10.01 g, 50 mmol) and bromoacetaldehyde diethyl acetal (7.52 ml, 50 mmol) in dimethylformamide (100 ml) was added potassium carbonate (10.37 g, 75 mmol) and the mixture was heated at 170° C. After 2.5 hr, the reaction mixture was cooled to room temperature. The mixture was diluted with water and ethyl acetate, and aqueous layer was removed. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 2-[4-(benzyloxy)phenoxy]acetaldehyde diethyl acetal (11.902 g, 75%, pale-brown oil).

Workup

temperaturethe reaction mixture was cooled to room temperature
customwas removed
washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-726b6d22575d4c52881cc2ca79325407
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410561B1

Reaction notes

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