Methylparaben → HCID 57340578, compound

HRID 895763Notes

Reaction equation

HRID 895763 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:12]1(O)[CH2:23][CH2:22]C[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CO>[CH:1]1([O:2][C:3](=[O:11])[C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=2)[CH2:22][CH2:23][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 7456MethylparabenHCID 15595Cyclododecanol2×

Product 1

HCID 57340578HCID 57340578, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

22.82 g (0.15 mol) p-hydroxybenzoic acid methyl ester, 55.30 g (0.30 mol) cyclododecanol and 28 mg (0.1 mmol) tetraisopropyl orthotitanate are placed under argon in a round-bottom flask with distillation bridge. The mixture is stirred and heated to 160° C. within one hour. On reaching this temperature the pressure is reduced to 900 mbar and during the further course of the reaction to 800 mbar, during which time methanol is removed by distillation. Stirring is continued for 5 hours at this temperature. A further 0.05 ml tetraisopropyl orthotitanate are added and the reaction mixture is stirred for a further 20 hours at 170° C. under normal pressure. The residue undergoes column chromatography (silica gel 60, 0040-0.063 mm, Merck). An n-hexane/acetone mixture (5:1) is used as eluent. The product obtained in this way is freed from adhering cyclododecanol under high vacuum at 140° C. The residue is recrystallised in acetone. 5.9 g (13%) in the form of colourless crystals are obtained:

Workup

  1. customis removed by distillation
  2. stirringStirring
  3. additionA further 0.05 ml tetraisopropyl orthotitanate are added
  4. stirringthe reaction mixture is stirred for a further 20 hours at 170° C. under normal pressure
  5. customThe product obtained in this way
  6. customat 140° C
  7. customThe residue is recrystallised in acetone
  8. custom5.9 g (13%) in the form of colourless crystals are obtained

Sources & evidence

ORD record
ord-c2721dbdd27f4eeb8243b609937af200
Source dataset
uspto-grants-2005_07
Patent number
US06916899B2

Reaction notes

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