Triethylamine → HCID 67586751, compound

HRID 1938125Notes

Reaction equation

HRID 1938125 reaction equation
[C:1]([C:4]1([OH:14])[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][CH:5]1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].CC1C=C(C(C)(C)C)[C:19]([OH:26])=[C:18]([C:27](C)(C)C)[CH:17]=1.C(N(CC)CC)C.CC(C(Cl)=O)=C>O1CCCC1>[C:1]([C:4]1([OH:14])[CH:12]=[C:11]([O:13][C:19](=[O:26])[C:18]([CH3:27])=[CH2:17])[CH:10]=[CH:9][CH:5]1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 67586083HCID 67586083, compound

Product 1

HCID 67586751HCID 67586751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-acetyl-4-hydroxysalicylic acid (15.0 millimole, 2.9 g) and butylhydroxytoluene (10 mg) was dissolved in tetrahydrofuran (THF). To the solution was added triethylamine (0.5 g), and the solution was cooled to 0° C. by ice bath. While stirring under a flow of nitrogen gas, methacryl chloride (20 millimole, 2.41 g) was added to the solution using a syringe over a period of 20 minutes, and the solution was kept stirred for another hour after completing the addition. After the reaction was over, the solvent was evaporated to give pale yellow powder. The powder was washed by dichloromethane and recrystallized by an aqueous solution of 0.5% hydroquinone. Dried under a reduced pressure, colorless crystal having a needle shape was obtained: m.p. 152.7° C.; yield 2.54 g, 64.1%.

Workup

  1. additionwas added to the solution
  2. customof 20 minutes
  3. additionthe addition
  4. customwas evaporated
  5. customto give pale yellow powder
  6. washThe powder was washed by dichloromethane
  7. customrecrystallized by an aqueous solution of 0.5% hydroquinone
  8. customDried under a reduced pressure, colorless crystal
  9. customwas obtained

Sources & evidence

ORD record
ord-d7f206f9c3b44f2380d6805538f76f78
Source dataset
uspto-grants-1997_12
Patent number
US05693320

Reaction notes

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