4'-Hydroxypropiophenone → 3-Chloro-4'-hydroxy-alpha-ethyl-benzhydrol

HRID 1980397Notes

Reaction equation

HRID 1980397 reaction equation
[Mg].[Cl:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[CH:7][CH:8]=1.O1CCCC1.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23][CH3:24])=[CH:18][CH:17]=1>C(O)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[C:22]([CH2:23][CH3:24])([OH:25])[C:19]1[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 62714'-HydroxypropiophenoneHCID 79281-Bromo-3-chlorobenzeneHCID 8028Tetrahydrofuran2×HCID 5462224Magnesium

Product 1

HCID 138824393-Chloro-4'-hydroxy-alpha-ethyl-benzhydrol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a Grignard reactant prepared from 14.6 g. of magnesium turnings and 115 g. of 3-chloro-bromobenzene in 350 ml. of dry tetrahydrofurane a solution of 30.1 g. of 4'-hydroxy-propiophenone in 540 ml. of dry tetrahydrofurane is added dropwise, with stirring under slight reflux. The reaction mixture is slightly boiled for 30 additional minutes, cooled and decomposed by pouring onto a mixture of ice and glacial acetic acid. After separation the organic phase is washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Crystallization of the solid residue from a mixture of n-hexane and ethyl acetate yields 42.6 g. of the named compound, melting at 132° to 134° C.

Workup

  1. temperaturecooled
  2. customAfter separation the organic phase
  3. washis washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customCrystallization of the solid residue
  7. additionfrom a mixture of n-hexane and ethyl acetate
  8. customyields 42.6 g

Sources & evidence

ORD record
ord-24eabe1ddb994cdaad21af9d566303ce
Source dataset
uspto-grants-1985_04
Patent number
US04508926

Reaction notes

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