Triethylamine → 2-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)

HRID 325121

Reaction equation

HRID 325121 reaction equation
[CH3:1][C:2]1([OH:12])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH:21]=[CH2:22]>C1COCC1>[C:20]([O:12][C:2]1([CH3:1])[CH:3]2[CH2:11][CH:7]3[CH2:6][CH:5]([CH2:10][CH:9]1[CH2:8]3)[CH2:4]2)(=[O:23])[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 1365452-Methyl-2-adamantanol

Product 1

HCID 112182922-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)Yield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-methyl-2-adamantanol (33 g, 0.2 mol) and triethylamine (0.22 mol) were dissolved in 300 ml of THF and then acryloyl chloride (19 g, 0.21 mol) was added slowly thereto using a dropping funnel. Then, the reaction was stirred at room temperature for about 12 hours. After completion of the reaction, excess THF was removed using a rotary evaporator and then the resultant product was poured into water. Then, the resultant product was neutralized with dilute sulfuric acid and extracted using diethyl ether and was then dried over magnesium sulfate. The diethyl ether removed crude product was vacuum-distilled to yield the desired product (yield: 80%).

Workup

  1. customwas removed
  2. customa rotary evaporator
  3. additionthe resultant product was poured into water
  4. extractionextracted
  5. dry with materialwas then dried over magnesium sulfate
  6. customThe diethyl ether removed crude product
  7. distillationwas vacuum-distilled

Sources & evidence

ORD record
ord-1f7d3f253df546a3a65ad0fd61105fcd
Source dataset
uspto-grants-2001_04
Patent number
US06222061B1

Linked notes

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