Bromobenzene → 1-Phenylcyclohexanol

HRID 1646235

Reaction equation

HRID 1646235 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[NH4+].[Cl-]>CCOCC>[C:2]1([C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 7967CyclohexanoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 153191-PhenylcyclohexanolYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard reagent resulting from the action of 48.9 g (0.3M) of bromobenzene on 8.75 g (0.35M) of magnesium in the form of turnings is prepared in 300 ml of anhydrous ether. To it is added 19.6 g (0.2M) of cyclohexanone dissolved in 300 ml of anhydrous ether. Stirring takes place for 3 h on the reflux condenser and the complex is decomposed by a cold, saturated NH4Cl solution and then, after settling, the liquids are extracted with ether (3×200 ml). The ethers are dried (Na2SO4) and evaporated in vacuo to give a yellowish solid which, after two crystallizations in petroleum ether, give 25 g of white 1-phenyl-cyclohexanol melting at 60° to 61° C. (IR).

Workup

  1. customfor 3 h
  2. extractionthe liquids are extracted with ether (3×200 ml)
  3. dry with materialThe ethers are dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give a yellowish solid which
  6. customafter two crystallizations in petroleum ether

Sources & evidence

ORD record
ord-2e502cc7b56043a3a0a042063670b8ab
Source dataset
uspto-grants-1993_01
Patent number
US05179109

Linked notes

Loading…