2-Methoxyethanol → HCID 54231349, compound

HRID 580967Notes

Reaction equation

HRID 580967 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[C-]#N.[Na+].[CH3:18][O:19][CH2:20]CO>>[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH2:12][CH2:18][O:19][CH3:20])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 8929Sodium CyanideHCID 4645407Methyl 4-(allyloxy)benzoate

Product 1

HCID 54231349HCID 54231349, compound

Procedure

A mixture of methyl 4-allyloxybenzoate (1.92 g), sodium cyanide (50 mg) and 2-methoxyethanol (20 ml) was heated at reflux for 24 hours. The mixture was evaporated to give an oil which was partitioned between dichloromethane and water. The organic phase was separated, washed with brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel using a 9:1 (v/v) mixture of pentane/ethyl acetate as eluent to give 2-methoxyethyl 4-allyloxybenzoate (1.7 g) as an oil; NMR(CDCl3): 3.44(3H,s), 3.72(2H,t), 4.44(2H,t), 4.55-4.64(2H,m), 5.27-5.48(2H,m), 5.96-6.14(1H,m), 6.93(2H,d) and 8.01(2H,d); m/z237(M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe mixture was evaporated
  4. customto give an oil which
  5. customwas partitioned between dichloromethane and water
  6. customThe organic phase was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was purified by flash column chromatography on silica gel using
  11. additiona 9:1 (v/v) mixture of pentane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-96c84a92bcd74f159fbb679c1fe39235
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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