(Diethoxymethyl)benzene → HCID 131710141, compound

HRID 1605820Notes

Reaction equation

HRID 1605820 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[CH2:25][C@:24]3([OH:26])[C@@:12]([CH:35]=[O:36])([C@@H:13]4[C@@H:21]([CH2:22][CH2:23]3)[C@:20]3([OH:27])[C@@:16]([CH3:34])([C@@H:17]([C:28]5[CH2:33][O:32][C:30](=[O:31])[CH:29]=5)[CH2:18][CH2:19]3)[CH2:15][CH2:14]4)[CH2:11][CH2:10]2)[CH2:5][C@H:4]([OH:37])[C@@H:3]1[OH:38].C(OC(OCC)C1C=CC=CC=1)C>>[CH:20](=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:12][CH:13]=1.[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[CH2:25][C@:24]3([OH:26])[C@@:12]([CH:35]=[O:36])([C@@H:13]4[C@@H:21]([CH2:22][CH2:23]3)[C@:20]3([OH:27])[C@@:16]([CH3:34])([C@@H:17]([C:28]5[CH2:33][O:32][C:30](=[O:31])[CH:29]=5)[CH2:18][CH2:19]3)[CH2:15][CH2:14]4)[CH2:11][CH2:10]2)[CH2:5][C@H:4]([OH:37])[C@@H:3]1[OH:38]

Participants

3

Reactant 2

HCID 69884(Diethoxymethyl)benzeneHCID 441860Helveticoside2×

Product 1

HCID 131710141HCID 131710141, compound

Conditions

Temperature
55 °C

Procedure

1.5 g. helveticoside are dissolved in 20 ml. benzaldehyde diethylacetal and treated with 1.5 g. of a cation exchanger (Lewatit S 100) in the H+-form. The mixture is heated to 55°C while stirring, and the course of the reaction is followed by thin-layer chromatography. After a reaction time of about 4 hours, no more helveticoside can be detected. The ion exchanger is filtered off and the solvent distilled off from the filtrate in a rotating evaporator under vacuum from a water pump. The residue is triturated with petroleum ether. Yield: 950 mg. benzaldehyde-helveticoside, melting point: 202°-210°C (decomposition)⟦alpha.D20 ] (C = 1, chloroform): +25° IR-bands: Aromatic bands at 3030, 3050, 695 and 755 cm-1. Lactone-carbonyl bands at 1740 and 1775 cm-1, aldehyde carbonyl band at 1719 cm-1, C = C double-bond band at 1618 cm-1. λ max. 207 mμ (in CH3OH).

Workup

  1. customAfter a reaction time of about 4 hours
  2. filtrationThe ion exchanger is filtered off
  3. distillationthe solvent distilled off from the filtrate in a rotating evaporator under vacuum from a water pump
  4. customThe residue is triturated with petroleum ether
  5. custom+25° IR-bands

Sources & evidence

ORD record
ord-d2b1db16c7d84836b7455a6be5e2743e
Source dataset
uspto-grants-1976_04
Patent number
US03951946

Reaction notes

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