Water → 4-Chloro-alpha-cyclopropylbenzenemethanol

HRID 561477Notes

Reaction equation

HRID 561477 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1([Mg]Br)[CH2:12][CH2:11]1.O.C(OCC)(=O)C>C(OCC)C.O1CCCC1>[CH:10]1([CH:6]([C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[OH:7])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 8857Ethyl AcetateHCID 178418630HCID 178418630, compound

Product 1

HCID 866794-Chloro-alpha-cyclopropylbenzenemethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.50 g (10.67 mmol) of 4-chlorobenzaldehyde were dissolved in 20 ml of diethyl ether at 0° C., and 32.0 ml (16.00 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were slowly added dropwise. Stirring at 0° C. for 1 h was followed by warming to RT, addition of water and ethyl acetate to the reaction solution, and separation of the phases. The organic phase was dried over sodium sulfate, the solid was filtered off, and the solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 1.21 g (62% of theory) of the title compound.

Workup

  1. temperatureby warming to RT
  2. customto the reaction solution, and separation of the phases
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationthe solid was filtered off
  5. customthe solvents were removed in vacuo
  6. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-08435c84eb8547068bae51e69d8422ee
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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