Acetic Acid → 1,3-dichloro-2-phenylpropan-2-ol

HRID 623201Notes

Reaction equation

HRID 623201 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][CH2:10][C:11]([CH2:13][Cl:14])=[O:12].C(O)(=O)C.O>CCOCC>[Cl:9][CH2:10][C:11]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([OH:12])[CH2:13][Cl:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 107931,3-DichloroacetoneHCID 178418255HCID 178418255, compound

Product 1

HCID 2325951,3-dichloro-2-phenylpropan-2-olYield 51%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

289 ml (0.866 mol) of a 3M solution of phenylmagnesium bromide in ether are run, over a period of 1.50 h, into a solution of 100 g (0.787 mol) of 1,3-dichloroacetone in 1000 ml of anhydrous ether under a nitrogen atmosphere and at -60° C. After 10 minutes, a solution of 83.5 g of acetic acid in 126 ml of ether is added to the reaction medium. The temperature is allowed to rise to +4° C. and 315 ml of water are run in. The ether phase is decanted, washed with water and dried over MgSO4. It is filtered, the filtrate is evaporated to dryness and the evaporation residue is distilled in vacuo to give 82.3 g (yield: 51%) of 1,3-dichloro-2-phenylpropan-2-ol. B.p. (0.5 mm Hg)=102° C. (0.5 mm Hg corresponds to 66.6 Pa).

Workup

  1. customto rise to +4° C.
  2. customThe ether phase is decanted
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationIt is filtered
  6. customthe filtrate is evaporated to dryness
  7. distillationthe evaporation residue is distilled in vacuo

Sources & evidence

ORD record
ord-303e9f8c26f547f6aa5457ef6fc92109
Source dataset
uspto-grants-1988_09
Patent number
US04774248

Reaction notes

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