Triethylamine → 2-Ethyltricyclo[3.3.1.1~3,7~]decan-2-yl prop-2-enoate

HRID 2298738Notes

Reaction equation

HRID 2298738 reaction equation
[CH2:1]([C:3]1([OH:13])[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)[CH3:2].C(N(CC)CC)C.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23]>CC(CC(C)C)=O>[C:21]([O:13][C:3]1([CH2:1][CH3:2])[CH:4]2[CH2:12][CH:8]3[CH2:7][CH:6]([CH2:11][CH:10]1[CH2:9]3)[CH2:5]2)(=[O:24])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 44019512-Ethyl-2-adamantanol

Product 1

HCID 221688802-Ethyltricyclo[3.3.1.1~3,7~]decan-2-yl prop-2-enoateYield 80%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
40 °C

Procedure

180 g of 2-Ethyl-2-adamantanol, 303 g of triethylamine and 500 g of methylisobutyl ketone were mixed by stirring at 40° C. While stirring, 136 g of acrylic acid chloride was added dropwise to the mixture. After completion of the dropwise addition, the mixture was stirred for three more hours. Then, extraction and distillation were conducted to obtain 2-ethyl-2-adamantyl acrylate at the yield of 80%.

Workup

  1. stirringWhile stirring
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred for three more hours
  4. extractionThen, extraction and distillation

Sources & evidence

ORD record
ord-f978f646b1ed48bebdf242c9bf9a7a76
Source dataset
uspto-grants-2002_12
Patent number
US06495307B2

Reaction notes

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