2,2-Dimethoxypropane → HCID 14768058, compound

HRID 2306091Notes

Reaction equation

HRID 2306091 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11]C(C=O)=[CH:7][CH:6]=1.[CH3:13][O:14][C:15]([O:18][CH3:19])([CH3:17])C>CO.C(Cl)Cl>[CH3:19][O:18][CH:15]([O:14][CH3:13])[C:17]1[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-

Product 1

HCID 14768058HCID 14768058, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxyethoxybenzaldehyde (Bernstein et aL, J. Am. Chem. Soc., 73: 906-912 (1951); 8.5 g, 51.2 mmol), 2,2-dimethoxypropane (30 mL, 244 mmol) in a mixture of methanol (40 mL) and CH2Cl2 (100 mL) was added anhydrous Amberlyst 15 (Aldrich) (1.0 g). The mixture was stirred for 5 hrs, the catalyst was removed by filtration and the filtrate was concentrated to give the crude product contaminated with the starting aldehyde. This material was chromatographed on silica eluting with 1:1 ethyl acetate-hexane. The pure product fractions were pooled and concentrated. Drying under vacuum afforded 7.6 g (70%) of the title compound as a pale yellow, viscous liquid. 1H NMR: d 7.28 (d, J=9 Hz, 2 H), 6.92 (d, J=9 Hz, 2H), 5.31 (s, 1H), 4.86 (t, J=5.5 Hz, 1H), 3.98 (t, J=5 Hz, 2H), 3.71 (q, J=5 Hz, 2H), 3.20 (s, 3H). 13C NMR: d 158.60, 130.19, 127.74, 113.90, 102.46, 69.43, 59.52, 52.27.

Workup

  1. additionwas added anhydrous Amberlyst 15 (Aldrich) (1.0 g)
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customto give the crude product
  5. customThis material was chromatographed on silica eluting with 1:1 ethyl acetate-hexane
  6. concentrationconcentrated
  7. customDrying under vacuum

Sources & evidence

ORD record
ord-d8f565feac6548fd903e3bcfd5b1718e
Source dataset
uspto-grants-2002_08
Patent number
US06441159B1

Reaction notes

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