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

HRID 1479246Notes

Reaction equation

HRID 1479246 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1.[CH2:13]1[O:15][CH2:14]1.B(F)(F)F.CCOCC>ClCCl.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH2:13][CH2:14][OH:15])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6354Ethylene Oxide2×HCID 8000Boron trifluoride etherateHCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a two-neck round bottom flask, which was equipped with a Dewar condenser, a solution of 4-hydroxymethylbenzoic acid methyl ester (2.50 g, 0.015 mol) in anhydrous dichloromethane (30 mL) was cooled to −10° C. in a salt/ice bath. 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. customTo a two-neck round bottom flask, which was equipped with a Dewar condenser
  2. stirringThe reaction mixture was stirred for 45 minutes
  3. extractionThe aqueous layer was extracted with dichloromethane (3 times)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide an oil
  8. customThe crude material was purified

Sources & evidence

ORD record
ord-d7b02cbce88c4b0685d864dbc7efaf96
Source dataset
uspto-grants-2016_08
Patent number
US09408927B2

Reaction notes

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