Hydrochloric Acid → 2-Chloro-1,1-bis(4-chlorophenyl)ethan-1-ol

HRID 1723067Notes

Reaction equation

HRID 1723067 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[Mg].[Cl:10][CH2:11][C:12]([O:14]CC)=O.[ClH:17]>CCOCC>[Br-:1].[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]([C:2]2[CH:7]=[CH:6][C:5]([Cl:17])=[CH:4][CH:3]=2)([OH:14])[CH2:11][Cl:10])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 7806p-BromochlorobenzeneHCID 5462224Magnesium

Product 2

HCID 259Bromide ionHCID 145187332-Chloro-1,1-bis(4-chlorophenyl)ethan-1-olYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Part A. A solution of 4-chlorobenzenemagnesium bromide was prepared in ether (800 mL) from 4-bromochlorobenzene (114.9 g, 0.6 mole) and magnesium chips (15.1 g, 0.62 mole). This mixture was cooled to 0°, and a solution of ethyl chloroacetate (24.5 g, 0.2 mole) was added dropwise. When addition was complete, stirring was continued at 0° for an additional hour. 1 N hydrochloric acid was then added, and the mixture extracted with dichloromethane. The organic phase was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was distilled in a kugelrohr apparatus at 0.1 torr and 180°-200° to provide 1,1-bis(4-chlorophenyl)-2-chloroethanol (43.1 g, 71%) as an oil. NMR(CDCl3) 7.33(8H,m) 4.11(2H,s) 3.17(1H,s). IR (neat film) 3551 cm-1.

Workup

  1. temperatureThis mixture was cooled to 0°
  2. additionWhen addition
  3. waitwas continued at 0° for an additional hour
  4. extractionthe mixture extracted with dichloromethane
  5. washThe organic phase was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residue was distilled in a kugelrohr apparatus at 0.1 torr and 180°-200°

Sources & evidence

ORD record
ord-19d044bdb81a453cb69f9690a0dc420f
Source dataset
uspto-grants-1989_08
Patent number
US04859693

Reaction notes

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