Triglyme → 2-Cyanomethoxy-3-methylbenzylalcohol

HRID 2117233Notes

Reaction equation

HRID 2117233 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) 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-e84e7450a7ac47cba8f48d97c6fa2cf7
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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