Water → 4-Benzyloxy-3-ethyl-5-methyl-benzonitrile

HRID 2069417Notes

Reaction equation

HRID 2069417 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[C:6]#[N:7])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(#N)C>[CH2:19]([O:11][C:10]1[C:9]([CH3:12])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:1][CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 597599503-Ethyl-4-hydroxy-5-methylbenzonitrile

Product 1

HCID 685070314-Benzyloxy-3-ethyl-5-methyl-benzonitrileYield 75.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3-Ethyl-4-hydroxy-5-methyl-benzonitrile (6.0 g, 37 mmol) is dissolved in acetonitrile (80 mL) and K2CO3 (10.1 g, 73 mmol) and benzyl bromide (6.56 g, 38 mmol) are added. The resulting suspension is stirred at 60° C. for 18 h, then water is added (100 mL) and the org. phase is collected. The aq. phase is extracted with EtOAc (100 mL) and the combined org. extracts are washed with water followed by brine, dried over MgSO4, filtered, evaporated and purified by CC (eluting with Heptane/EtOAc 9:1) to give 4-benzyloxy-3-ethyl-5-methyl-benzonitrile as a yellow oil (7.02 g); LC-MS: tR=1.11 min, [M+H]+=293.16.

Workup

  1. customphase is collected
  2. extractionThe aq. phase is extracted with EtOAc (100 mL)
  3. washextracts are washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by CC (eluting with Heptane/EtOAc 9:1)

Sources & evidence

ORD record
ord-13dca4e4ff2b4426bdd86ed59b7a46fd
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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