Cyclohexane, 1,1-diethoxy- → HCID 131710139, compound

HRID 1283369Notes

Reaction equation

HRID 1283369 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(OC1(OCC)CCCCC1)C>>[C:9]1(=[O:8])[CH2:25][CH2:24][CH2:12][CH2:11][CH2:10]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 74279Cyclohexane, 1,1-diethoxy-HCID 441860Helveticoside2×

Product 1

HCID 131710139HCID 131710139, compound

Conditions

Temperature
55 °C

Procedure

1.5 g. helveticoside are dissolved in 20 ml. cyclohexanone diethylketal and mixed with 1.5 g. of a cation exchanger in the H+ form (e.g. the ion exchanger known by the trade name of Lewatit S 100). The mixture is heated to 55°C while stirring, and the course of the reaction is followed by thin-layer chromatography. After about 4 hours of reaction 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: 850 mg. cyclohexanone-helveticoside.

Workup

  1. filtrationThe ion exchanger is filtered off
  2. distillationthe solvent distilled off from the filtrate in a rotating evaporator under vacuum from a water pump
  3. customThe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-20b15f94d38d4df99a1b89a0bd15b2fc
Source dataset
uspto-grants-1976_08
Patent number
US03975373

Reaction notes

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