Ethylene Glycol → 2-Vinylbenzaldehyde ethylene acetal

HRID 1418364Notes

Reaction equation

HRID 1418364 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])=[CH2:2].C[Si](Cl)(C)C.[CH2:16](O)[CH2:17][OH:18]>C(=O)(O)[O-].[Na+]>[CH2:17]1[O:18][CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[CH:1]=[CH2:2])[O:6][CH2:16]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 39391Benzaldehyde, 2-ethenyl-

Product 1

HCID 570815972-Vinylbenzaldehyde ethylene acetal

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-vinylbenzaldehyde (2.9 g, 22 mmol) and trimethylsilyl chloride (11 ml) in ethylene glycol (95 ml) was stirred for 16 h, diluted with saturated sodium bicarbonate solution, extracted with ether, dried over sodium sulphate and evaporated to afford a colourless oil (2.7 g), MS (+EI) 176 (M+), 1H NMR (CDCl3) 7.57 (1H, m), 7.53 (1H, dd, J1.5, 7.5 Hz), 7.36-7.30 (2H, m), 7.14 (1H, dd, J11, 17.4 Hz), 6.04 (1H, s) 5.69 (1H, dd, J1.3, 17.4 Hz), 5.34 (1H, dd, J1.3, 11.0 Hz), 4.18-4.04 (2H, m), 3.77-3.65 (2H, m).

Workup

  1. extractionextracted with ether
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-af51443a925a48a791f16128fb1ca950
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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