Triglyme → 2-Cyanomethoxy-3-methylbenzylalcohol

HRID 892151Notes

Reaction equation

HRID 892151 reaction equation
COCCOCCOCCOC.[BH4-].[Na+].[C:15]([CH2:17][O:18][C:19]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[O:22])#[N:16]>C1COCC1>[OH:22][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:19]=1[O:18][CH2:17][C:15]#[N:16]

Participants

5

Reactant 3

HCID 8189TriglymeHCID 4311764Sodium borohydrideHCID 222413452-(2-Formyl-6-methylphenoxy)acetonitrile

Product 1

HCID 222413612-Cyanomethoxy-3-methylbenzylalcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 2M triglyme solution of sodium borohydride (16.0 mL, 32.1 mmoles) is slowly added to a cooled (−78° C.) solution of 2-cyanomethoxy-3-methylbenzaldehyde (11.25 g, 64.2 mmoles, example 22) in THF (180 mL). After stirring for one hour, the reaction is warmed to 0° C. for two hours, then quenched with 2N HCl (16.8 mL) and diluted with ether. The organic layer is isolated and washed with twice with distilled water and brine, then dried over MgSO4. The organic solution is concentrated to give the title compound as a yellow oil.

Workup

  1. customquenched with 2N HCl (16.8 mL)
  2. additiondiluted with ether
  3. customThe organic layer is isolated
  4. washwashed with twice with distilled water and brine
  5. dry with materialdried over MgSO4
  6. concentrationThe organic solution is concentrated

Sources & evidence

ORD record
ord-81d731c48e064f0e90f6af35ecba6851
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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