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

HRID 646502Notes

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 1MHCl (aq) then extracted in to ethyl acetate. The organic phases were combined and washed again with 1MHCl (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 1MHCl (aq)
extractionthen extracted in to ethyl acetate
washwashed again with 1MHCl (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-49cf99a6076a434ab3e0224d816380f8
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705027B2

Reaction notes

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