Bromobenzene → 2-chloro-1,1-diphenylethanol

HRID 1583325Notes

Reaction equation

HRID 1583325 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH2:9]([Cl:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[Cl-].[NH4+]>[Na].C(OCC)C>[C:2]1([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[CH2:9][Cl:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 107572-ChloroacetophenoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×

Product 1

HCID 2325962-chloro-1,1-diphenylethanolYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5360545SodiumSolvent

Procedure

Bromobenzene (0.2 mol, 31.4 g) in sodium dry diethyl ether (200 ml) was added dropwise to magnesium (0.22 gram atoms, 5.3 g ). After all the magnesium had reacted, phenacyl chloride (0.1 mol, 15.5 g) in diethyl ether (100 ml) was added dropwise and the solution stirred at room temperature for 1 hour. The reaction mixture was poured into saturated ammonium chloride solution, washed with water (3×150 ml), and dried (Na2SO4). Removal of the ether gave a pale yellow oil which solidified on standing. Recrystallisation from petroleum ether (60°-80°) gave 1,1-diphenyl-2-chloroethan-1-ol (60%) as a white crystalline solid, m.p. 56°-57°.

Workup

  1. washwashed with water (3×150 ml)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the ether
  4. customgave a pale yellow oil which
  5. customRecrystallisation from petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-c3199c8677c84bd0bafb899bd88e3dc2
Source dataset
uspto-grants-1985_11
Patent number
US04551469

Reaction notes

Loading…