4'-Hydroxypropiophenone → HCID 20402926, compound

HRID 1980400Notes

Reaction equation

HRID 1980400 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Li])=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][CH:11]=1.O1CCCC1>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]([CH2:17][CH3:18])([OH:19])[C:13]2[CH:12]=[CH:11][C:10]([OH:9])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 62714'-HydroxypropiophenoneHCID 8028TetrahydrofuranHCID 178506657HCID 178506657, compound

Product 1

HCID 20402926HCID 20402926, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 400 ml. of a 0.5 molar ethereal 4-bromophenyl-lithium solution a solution of 7.5 g. of 4'-hydroxy-propiophenone in 37 ml. of dry tetrahydrofurane is added dropwise, with stirring at a temperature between -50° C. and -40° C. The reaction mixture is stirred at 0° C. for an additional hour, and is then decomposed with a mixture of ice and glacial acetic acid. The aqueous phase is extracted with ether, the ethereal phases are combined, and washed to neutral with water. After drying over anhydrous magnesium sulfate the solvent is distilled off under reduced pressure, and the residue is chromatographed on a silica gel column with a 7:3 mixture of benzene and ethyl acetate as an eluting agent. The solvent is distilled off in vacuo, and the residue is crystallized from a mixture of ethyl acetate and dichloromethane. 4.2 g. of the named compound are obtained, melting at 161° to 162° C.

Workup

  1. stirringThe reaction mixture is stirred at 0° C. for an additional hour
  2. extractionThe aqueous phase is extracted with ether
  3. washwashed to neutral with water
  4. dry with materialAfter drying over anhydrous magnesium sulfate the solvent
  5. distillationis distilled off under reduced pressure
  6. customthe residue is chromatographed on a silica gel column with a 7:3 mixture of benzene and ethyl acetate as an eluting agent
  7. distillationThe solvent is distilled off in vacuo
  8. customthe residue is crystallized from a mixture of ethyl acetate and dichloromethane
  9. customof the named compound are obtained

Sources & evidence

ORD record
ord-4538f889c9fe4dc5a4348892958c0548
Source dataset
uspto-grants-1985_04
Patent number
US04508926

Reaction notes

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