Ethylene Glycol → HCID 57602458, compound

HRID 1787945Notes

Reaction equation

HRID 1787945 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:13])[CH3:12])[CH:6]=1.[CH2:14](O)[CH2:15][OH:16]>C1C=CC=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>[CH3:12][C:11]1([C:7]2[CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:10]=[CH:9][CH:8]=2)[O:16][CH2:15][CH2:14][O:13]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 143614871-[3-(Methoxymethoxy)phenyl]ethan-1-one

Product 1

HCID 57602458HCID 57602458, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 241BenzeneSolvent

Procedure

A mixture of 3-(acetyl)phenyl methoxymethyl ether (3.6 g, 20 mmol), ethylene glycol (3.72 g, 60 mmol) and pyridinium tosylate (0.075 g, 0.3 mmol, 3 mol %) in benzene (200 mL) was azeotropically refluxed for 8 h. The reaction was concentrated and the resulting residue was diluted with ethyl ether (150 mL) and washed with saturated aqueous bicarbonate (2×50 mL) and brine (100 mL). The ethyl ether solution was dried (K2CO3) and concentrated. The residue was suspended in n-hexanes and the by-product was precipitated. The n-hexane solution was then separated and concentrated to obtain the desired product (2.69 g, 61%); TLC Rf: 0.5 (30% EtOAc/n-hexanes).

Workup

  1. temperaturewas azeotropically refluxed for 8 h
  2. concentrationThe reaction was concentrated
  3. additionthe resulting residue was diluted with ethyl ether (150 mL)
  4. washwashed with saturated aqueous bicarbonate (2×50 mL) and brine (100 mL)
  5. dry with materialThe ethyl ether solution was dried (K2CO3)
  6. concentrationconcentrated
  7. customthe by-product was precipitated
  8. customThe n-hexane solution was then separated
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-88b026a5d5ba4f24b8b105d199c7161c
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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