p-Toluenesulfonic acid → Hydroxycitronellal dimethyl acetal

HRID 1576988

Reaktionsgleichung

Reaktionsgleichung von HRID 1576988
[CH2:1]([O:3]C(=O)C=C(C)C=CCC(C)CCCC(C)(OCC#C)C)C.[CH3:24][CH:25]([CH2:33][CH:34]=[O:35])[CH2:26][CH2:27][CH2:28][C:29]([OH:32])([CH3:31])[CH3:30].[CH3:36]OC(O)O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(=O)C.[Na+]>CO>[CH3:36][O:35][CH:34]([O:3][CH3:1])[CH2:33][CH:25]([CH3:24])[CH2:26][CH2:27][CH2:28][C:29]([CH3:31])([OH:32])[CH3:30]

Komponenten

7

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 7888HydroxycitronellalHCID 517045Sodium AcetateHCID 5231663Methanediol, methoxy-HCID 53869178HCID 53869178, Verbindung

Produkt 1

HCID 8863Hydroxycitronellal dimethyl acetal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The starting material of Example 1 can be prepared as follows: 172.2 g. of hydroxycitronellal and 106.1 g. of orthoformic acid methyl ester are treated dropwise, while cooling with ice, with a solution of 0.5 g. of p-toluenesulphonic acid in 800 ml. of absolute methanol. After 2 hours, 5 g. of sodium acetate are added and the mixture is concentrated on a rotary evaporator at 50°C. Upon distillation, the residue yields pure 1,1-dimethoxy-3,7-dimethyl-7-octanol; boiling point = 102°C/0.4 mmHg; nD22 = 1.4400.

Aufarbeitung

  1. temperaturewhile cooling with ice, with a solution of 0.5 g
  2. concentrationthe mixture is concentrated on a rotary evaporator at 50°C
  3. distillationUpon distillation

Quellen und Nachweise

ORD-Eintrag
ord-2303cff94e6946bea6d46d04544a1a1c
Quelldatensatz
uspto-grants-1976_09
Patentnummer
US03983247

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