4'-Chloropropiophenone → 1-Cyclopropyl-1-(4-chlorophenyl)propanol

HRID 561469Notes

Reaction equation

HRID 561469 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[CH:12]1([Mg]Br)[CH2:14][CH2:13]1.C1(C(C2C=CC(Cl)=CC=2)(O)C)CC1>O1CCCC1>[CH:12]1([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:11])[CH2:9][CH3:10])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 226974'-ChloropropiophenoneHCID 234634-Chloro-alpha-cyclopropyl-alpha-methylbenzenemethanolHCID 178418630HCID 178418630, compound

Product 1

HCID 583925071-Cyclopropyl-1-(4-chlorophenyl)propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared starting from 1.50 g (8.90 mmol) of 1-(4-chlorophenyl)propan-1-one and 35.6 ml (17.79 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran in analogy to the synthesis of the compound from Example 138A. 1.42 g (76% of theory) of the title compound were obtained.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6003ee12bd584f2b9382fe164d648bb4
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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