Triethylamine → HCID 15509192, compound

HRID 1355318Notes

Reaction equation

HRID 1355318 reaction equation
[CH:1]1([C:7]2([OH:12])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:13](Cl)(=[O:16])[CH:14]=[CH2:15].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:13]([O:12][C:7]1([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:8][CH2:9][CH2:10][CH2:11]1)(=[O:16])[CH:14]=[CH2:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 127317841-Cyclohexylcyclopentan-1-ol

Product 1

HCID 15509192HCID 15509192, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 1 liter of methylene chloride was dissolved 92.4 g of 1-cyclohexylcyclopentanol. To the solution below −20° C., 74.3 g of acrylic chloride was added dropwise over 10 minutes. To the reaction mixture, 1.0 g of 4-(N,N-dimethylamino)pyridine was added and then, 125.0 g of triethylamine was added dropwise over one hour and below −20° C. This reaction mixture was agitated for 15 hours at room temperature and subjected to conventional post-treatment, obtaining an oily substance. Vacuum distillation yielded 110.5 g of 1-cyclohexylcyclopentyl acrylate (designated Monomer 1). The yield was 90.5%. Boiling point: 83-85° C./53.3 Pa

Workup

  1. customobtaining an oily substance
  2. distillationVacuum distillation

Sources & evidence

ORD record
ord-ab8c5eefc88f4be8831911a5308e1bdd
Source dataset
uspto-grants-2003_07
Patent number
US06586157B2

Reaction notes

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