Tetrahydrofuran → 2-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethyl methacrylate

HRID 1801435Notes

Reaction equation

HRID 1801435 reaction equation
[CH3:1][C:2]1([O:12][C:13](=[O:20])[CH2:14][O:15][C:16](=[O:19])[CH2:17][OH:18])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.O1CCCC1.C(N(CC)CC)C.[C:33](Cl)(=[O:37])[C:34]([CH3:36])=[CH2:35]>COC1C=CC(O)=CC=1.C(OCC)C>[C:33]([O:18][CH2:17][C:16]([O:15][CH2:14][C:13]([O:12][C:2]1([CH3:1])[CH:9]2[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]1[CH2:11]3)[CH2:10]2)=[O:20])=[O:19])(=[O:37])[C:34]([CH3:36])=[CH2:35]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 581059672-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanol

Product 1

HCID 578287412-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethyl methacrylateYield 97%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 3283Diethyl EtherSolvent

Procedure

165 g (584 mmol) of 2-(2-(2-methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanol, 2,000 mL, of tetrahydrofuran (THF), 105 mL (754 mmol) of triethylamine, and 0.165 g (1,000 ppm) of p-methoxyphenol were added to and dissolved in a 2 L three-necked flask equipped with a thermometer, a cooling pipe, and a stirrer. Then, 62.7 mL (648 mmol) of methacryloyl chloride was gradually added thereto while cooling in an ice bath. The temperature of the resultant was elevated to room temperature, and the resultant was stirred for 3 hours. Following completion of the reaction, 1,000 mL of diethyl ether was added thereto, followed by washing with 200 mL of distilled water 5 times. Thereafter, the extraction liquid was concentrated, thereby obtaining 198 g of an objective compound in the form of a colorless liquid (yield: 97%, GC purity: 99%).

Workup

  1. dissolutiondissolved in a 2 L three-necked flask
  2. customequipped with a thermometer
  3. temperaturewhile cooling in an ice bath
  4. customwas elevated to room temperature
  5. additionwas added
  6. washby washing with 200 mL of distilled water 5 times
  7. extractionThereafter, the extraction liquid
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-512291c925104378b51b583b2db7fae5
Source dataset
uspto-grants-2013_01
Patent number
US08349534B2

Reaction notes

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