Hydrogen Bromide → 1-Propyl-4-p-propylphenylcyclohexan-1-ol

HRID 1980463Notes

Reaction equation

HRID 1980463 reaction equation
Br.[CH2:2]([C:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)[CH2:7][CH:6]=1)[CH2:3][CH3:4].C(C1C=CC(C2CCC(=[O:35])CC2)=CC=1)CC.C([Mg]Br)CC>C(Cl)Cl>[CH2:17]([C:14]1([OH:35])[CH2:15][CH2:16][CH:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=2)[CH2:12][CH2:13]1)[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 144957544-(4-Propylphenyl)cyclohexan-1-oneHCID 198193641-Propyl-4-p-propylphenylcyclohexeneHCID 178455851HCID 178455851, compound

Product 1

HCID 198194031-Propyl-4-p-propylphenylcyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HBr is passed, at 0°, into a solution in 50 ml of CH2Cl2 of 2.42 g of 1-propyl-4-p-propylphenylcyclohexene (obtainable by reacting 4-p-propylphenylcyclohexanone with C3H7MgBr, hydrolysing the product to give 1-propyl-4-p-propylphenylcyclohexan-1-ol and dehydrating the latter), the mixture is allowed to stand overnight and is worked up in the customary manner to give r-1-bromo-1-propyl-cis-4-p-propylphenylcyclohexane.

Sources & evidence

ORD record
ord-33d78d782a8f4fe9aeea0e8f7d60b1b7
Source dataset
uspto-grants-1985_04
Patent number
US04510069

Reaction notes

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