Water → HCID 21465386, compound

HRID 1939947Notes

Reaction equation

HRID 1939947 reaction equation
[CH3:1][Mg]Br.[C:4]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])#[N:5].O>O1CCCC1>[C:4]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]([OH:9])[CH3:1])#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 1012092-CyanobenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 21465386HCID 21465386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of methylmagnesium bromide in tetrahydrofuran (12 ml, 12 mmol) was dropwise and portionwise added to a solution of 2-cyanobenzaldehyde (1.31 g, 10.0 mmol) dissolved in dried tetrahydrofuran (25 ml), followed by stirring at room temperature for one night. After the reaction, water was added to the reaction mixture followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the drying agent was filtered off, and the solution was concentrated under reduced pressure to give 1-(2-cyanophenyl)ethanol (1.47 g, quantitative).

Workup

  1. additionwas added to the reaction mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe drying agent was filtered off
  5. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f73fdb902c8e458ea82ea0a85b387471
Source dataset
uspto-grants-1997_12
Patent number
US05698560

Reaction notes

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