Bromobenzene → 2-chloro-1,1-diphenylethanol

HRID 1638485Notes

Reaction equation

HRID 1638485 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 to 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 the petroleum ether (60°-80°) gave 1,1-diphenyl-2-chloro-ethan-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 the petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-c451265250e440e9b258937ea8190a54
Source dataset
uspto-grants-1989_11
Patent number
US04880457

Reaction notes

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