Ethylene Oxide → Methyl 4-((2-hydroxyethoxy)methyl)benzoate

HRID 1516051Notes

Reaction equation

HRID 1516051 reaction equation
[CH2:1]1[O:3][CH2:2]1.B(F)(F)F.C[CH2:9][O:10]CC.[CH3:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:18]([O:21][CH2:22]C)(=[O:20])[CH3:19]>[Cl-].[Na+].O>[CH3:22][O:21][C:18](=[O:20])[C:19]1[CH:17]=[CH:16][C:15]([CH2:1][O:3][CH2:2][CH2:9][OH:10])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6354Ethylene Oxide2×HCID 8000Boron trifluoride etherateHCID 8003PentaneHCID 8857Ethyl Acetate

Product 1

HCID 23344083Methyl 4-((2-hydroxyethoxy)methyl)benzoateYield 17%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Ethylene oxide (1.10 mL) was added to the cooled stirring solution dropwise followed by the addition of boron trifluoride etherate (0.51 ml). The reaction mixture was stirred for 45 minutes and then warmed to room temperature for 30 minutes to boil off any excess of ethylene oxide in the reaction mixture. The reaction mixture was then diluted with brine. The aqueous layer was extracted with dichloromethane (3 times). All of the organic layers were combined, dried over Na2SO4, filtered, and concentrated to provide an oil. The crude material was purified using silica gel:chromatography (4:1 pentane:ethyl acetate) to provide the desired product (537 mg, 2.56 mmol) in 17% yield. 1H (CDCl38.36, 600 Mhz): δ (2H, d, J=8.4 Hz), 7.41 (2H, d, J=8.5 Hz), 4.62 (3H, s), 3.92 (2H, s), 3.78 (m, 2H), 3.63 (2H, m); 13C (CDCl3167.1, 143.5, 130.0, 129.8, 127.5, 72.9, 72.0, 150 MHz): δ 62.1, 52.3.

Workup

  1. stirringThe reaction mixture was stirred for 45 minutes
  2. extractionThe aqueous layer was extracted with dichloromethane (3 times)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide an oil
  7. customThe crude material was purified

Sources & evidence

ORD record
ord-9647fd8086bc4fa3be819c3ed0c6fe27
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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