Acetic Acid → HCID 19786906, compound

HRID 263923Notes

Reaction equation

HRID 263923 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[C:8]([C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])C=O)([CH3:11])([CH3:10])[CH3:9].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:11][C:8]([C:12]1[CH:13]=[C:14]([C:2](=[CH2:1])[C:3]([OH:5])=[O:4])[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 19786906HCID 19786906, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of malonic acid (Aldrich, 4.36 g, 41.9 mmol), 3,5-di-tert-butyl-4-hydroxybenzaldehyde (Aldrich, 5.00 g, 20.9 mmol), piperidine (Aldrich, 0.18 g, 2.10 mmol) and acetic acid (0.13 g, 2.10 mmol) in toluene (100 mL) was warmed at reflux (water removed using a Dean-Stark trap). After 5.5 h malonic acid was added (4.36 g, 41.9 mmol) and the reaction mixture was warmed at reflux for 12 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was chromatographed (SiO2, flash, methanol-methylene chloride, 5:95) to give 2.43 g (42.1% yield of (E)-1-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl propenoic acid as a white solid.

Workup

  1. customremoved
  2. additionAfter 5.5 h malonic acid was added (4.36 g, 41.9 mmol)
  3. temperaturethe reaction mixture was warmed
  4. temperatureat reflux for 12 h
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed (SiO2, flash, methanol-methylene chloride, 5:95)

Sources & evidence

ORD record
ord-438ae82b0a104bc4beb18c92bacac370
Source dataset
uspto-grants-1997_07
Patent number
US05646149

Reaction notes

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