Ethylene Glycol → HCID 18715593, compound

HRID 1406676Notes

Reaction equation

HRID 1406676 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:16](O)[CH2:17][OH:18]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[C:8]1([C:6]2([C:5]3[CH:14]=[CH:15][C:2]([CH3:1])=[CH:3][CH:4]=3)[O:18][CH2:17][CH2:16][O:7]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 86524-Methylbenzophenone

Product 1

HCID 18715593HCID 18715593, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a round-bottom flask were added 4-methylbenzophenone (11, 5.0 g, 25.5 mmol, 1.0 equiv.), ethylene glycol (57 mL, 1020 mmol, 40.0 equiv.), para-toluenesulfonic acid monohydrate (147 mg, 0.77 mmol, 0.03 equiv.), and toluene (65 mL, 0.4 M). The biphasic reaction mixture was stirred vigorously at reflux with a Dean-Stark trap for 4 days. The reaction mixture was cooled to room temperature. The reaction mixture was washed with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), dried over Mg504, filtered, and concentrated. Recrystallization from hexanes yielded 12 (4.58 g, 75%) as a white solid. 1H-NMR (500 MHz, CDCl3) δ 7.58-7.55 (m, 2H), 7.45-7.40 (d, 2H, J=8.0 Hz), 7.38-7.35 (m, 2H), 7.33-7.30 (m, 1H), 7.18 (d, 2H, J=8.0 Hz), 4.09 (s, 4H), 2.37 (s, 3H). 13C-NMR (125 MHz, CDCl3): δ 142.2, 139.1, 137.7, 128.7, 128.0, 127.9, 126.1, 126.0, 109.4, 64.8, 21.1.

Workup

  1. customThe biphasic reaction mixture
  2. temperatureat reflux with a Dean-Stark trap for 4 days
  3. washThe reaction mixture was washed with saturated NaHCO3 (2×50 mL) and brine (2×50 mL)
  4. customdried over Mg504
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-f754f73eb06741f6a5865b7cba9757c0
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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