2-(Phenylmethylene)octanal → HCID 54380108, compound

HRID 1589710Notes

Reaction equation

HRID 1589710 reaction equation
[CH2:1]([C:7](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:8]=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(OCC)(OCC)OCC.[C:27]([C@@H:32]([C@H:34]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[OH:35])O)([O:29][CH2:30][CH3:31])=[O:28]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:10](=[C:7]([CH:8]1[O:35][C@@H:34]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C@H:32]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[O:9]1)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 75852-(Phenylmethylene)octanalHCID 31214Ethyl orthoformateHCID 6993580Diethyl tartrate

Product 1

HCID 54380108HCID 54380108, compoundYield 108.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of α-hexylcinnamaldehyde (62.19 g, 0.288 mole), triethyl orthoformate (42.61 g, 0.288 mole), diethyl L-tartrate (51.5 g, 0.25 mole) in toluene (180 ml) containing p-toluene sulfonic acid (0.8 g) was refluxed for 1 hour. About 100 ml of ethanol-toluene mixture was distilled over a period of 2 hours, and after cooling the remaining solvent was removed on a rotary evaporator. The residue was dissolved in toluene (200 ml) and the solution was washed with aqueous NaHCO3 and then with water. The solution was dried over Na2SO4, and the solvent was evaporated under reduced pressure to provide a brown liquid (110.1 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. distillationAbout 100 ml of ethanol-toluene mixture was distilled over a period of 2 hours
  3. temperatureafter cooling the remaining solvent
  4. customwas removed on a rotary evaporator
  5. dissolutionThe residue was dissolved in toluene (200 ml)
  6. washthe solution was washed with aqueous NaHCO3
  7. dry with materialThe solution was dried over Na2SO4
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-47128afd3401485fa6719e7e6b842d65
Source dataset
uspto-grants-1993_04
Patent number
US05199450

Reaction notes

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