Hydrochloric Acid → 2-chloro-1,1-diphenylethanol

HRID 2198533Notes

Reaction equation

HRID 2198533 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O[C:12](=[O:15])[CH2:13][Cl:14])C.Cl>CCOCC>[Cl:14][CH2:13][C:12]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 7961BromobenzeneHCID 5462224Magnesium

Product 1

HCID 2325962-chloro-1,1-diphenylethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

15 g of magnesium chips are reacted with 94.2 g of bromobenzene in 250 ml of absolute ether at 30° to 35° C., followed by the dropwise addition over a period of 30 minutes at 0° to 10° C. of 24.5 g of chloroacetic acid ethyl ester. After stirring for 1 hour, the reaction mixture is poured onto ice, acidified with dilute hydrochloric acid and extracted by shaking with methylene chloride. The organic phase is washed twice with water, subsequently dried over sodium sulphate and concentrated in vacuo. The oily residue is distilled in a high vacuum at 135°-140° C./0.03 Torr. 2-Chloro-1,1-diphenyl-ethan-1-ol melting at 64° to 66° C. is obtained in a yield of 32.8 g.

Workup

  1. additionthe reaction mixture is poured onto ice
  2. extractionextracted
  3. stirringby shaking with methylene chloride
  4. washThe organic phase is washed twice with water
  5. dry with materialsubsequently dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. distillationThe oily residue is distilled in a high vacuum at 135°-140° C./0.03 Torr

Sources & evidence

ORD record
ord-e38ea7197a3247488ccba03e3b665875
Source dataset
uspto-grants-1982_11
Patent number
US04358458

Reaction notes

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