Ethanol → 3-Chloro-5-(hydroxymethyl)benzonitrile

HRID 1260894Notes

Reaction equation

HRID 1260894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)[C:5]([O-])=[O:6].C(O)C.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:11]#[N:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 86314132HCID 86314132, compound

Product 1

HCID 583695423-Chloro-5-(hydroxymethyl)benzonitrileYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

(Step 2) To a mixed solution of 3-chloro-5-cyanobenzoate (1.13 g) obtained in Step 1 in tetrahydrofuran:ethanol=10:1 (33 ml) was added lithium tetrahydroborate (0.19 g) at 0° C. After stirring at 60° C. for 2 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1) to give 3-chloro-5-(hydroxymethyl)benzonitrile (0.60 g) as a white solid.

Workup

  1. customthe reaction solution was quenched with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-abf171aa4a4147019f76868aa8a472f2
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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