Benzyl Bromide → HCID 18973793, compound

HRID 2395008Notes

Reaction equation

HRID 2395008 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C(C(C)(C)C)=O)=[CH:4][C:3]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(OCC)(=O)C>CN(C=O)C.O>[CH2:33]([O:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:25][CH:26]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18973738HCID 18973738, compound

Product 1

HCID 18973793HCID 18973793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-[3-(2-hydroxy-5-(t-butylcarbonyloxy)phenyl)propyl]benzoic acid (3 g) and potassium carbonate (3.5 g) in DMF (10 ml) was added benzyl bromide (2.97 ml). The mixture was stirred for 18 hours, poured into ethyl acetate (100 ml) and water (100 ml). The organic solution was washed with brine (100 ml), dried (magnesium sulphate) filtered and evaporated. The residue was purified by subjecting to chromatography on silica gel using ethyl acetate:hexane (1:9) as eluant. There was thus obtained benzyl 4-[3-(2-benzyloxy-5-(t-butylcarbonyloxy) phenyl)propyl]benzoate (2 g)

Workup

  1. washThe organic solution was washed with brine (100 ml)
  2. dry with materialdried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-3c0059e40d894be89c787feca17ec0ee
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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