Benzyl Bromide → 1-(2,4-Bis(benzyloxy)-5-isopropylphenyl)ethanone

HRID 2097288Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH2:12][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

1-(2,4-Dihydroxy-5-isopropyl-phenyl)ethanone (1 eq) was dissolved in DMF and potassium carbonate (2.2 eq) then benzyl bromide (2.2 eq) were added. The suspension was heated, with stirring to 150° C., under nitrogen, for 16 hrs. The solution was cooled to room temperature and the mixture was poured into 1 MHCl (aq) then extracted in to ethyl acetate. The organic phases were combined and washed again with 1 MHCl (aq) then five times with brine solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo, to give a solid, which was purified by diethyl ether:hexane (1:1) trituration to give 1-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-ethanone.

Workup

temperatureThe suspension was heated
temperatureThe solution was cooled to room temperature
additionthe mixture was poured into 1 MHCl (aq)
extractionthen extracted in to ethyl acetate
washwashed again with 1 MHCl (aq)
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a solid, which
customwas purified by diethyl ether:hexane (1:1) trituration

Sources & evidence

ORD record: ord-ec8fe1925c8a487481d5587b24f8940d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450310B2

Reaction notes

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