Dichloromethane → (1-Naphthyl)ethyl Methacrylate

HRID 2373123Notes

Reaction equation

HRID 2373123 reaction equation
[C:1]1([CH2:11][CH2:12][OH:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClCCl.[C:24](Cl)(=[O:28])[C:25]([CH3:27])=[CH2:26]>CN(C)C1C=CN=CC=1.C(OCC)C>[C:24]([O:13][CH2:12][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:28])[C:25]([CH3:27])=[CH2:26]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13047Naphthalen-1-ethanolHCID 13528Methacryloyl chloride

Product 1

HCID 3316929(1-Naphthyl)ethyl Methacrylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-(1-naphthy)ethanol (30.0 g, 174 mmol), triethylamine (24.2 g, 239 mmol), 4-(dimethylamino)pyridine (1.1 g, 9.1 mmol), and dichloromethane (500 mL) was treated dropwise under nitrogen with methacryloyl chloride (18.9 g, 181 mmol), and then heated at refluxed for 4 h. The reaction mixture was cooled to ambient and diluted with diethyl ether. The solution was filtered and the filtrate was washed twice with water, once with NaHCO3, and once with brine. The solution was dried (Na2SO4) and concentrated to deposit a yellow oil. The product was purified by distillation at reduced pressure, collecting the fraction bp 120-125° C./0.08 mm to provide a colorless oil, mass: 36.0 g (86% theory). 1H (CDCl3): δ 2.00 (s, 3H), 3.50 (t, 2H), 4.55 (t, 2H), 5.60 (s, 1H), 6.15 (s, 1H), 7.50 (m, 4H), 7.8 (d, 1H), 7.9 (d, 1H), 8.2 (d, 1H).

Workup

  1. temperatureheated
  2. temperatureat refluxed for 4 h
  3. temperatureThe reaction mixture was cooled to ambient and
  4. filtrationThe solution was filtered
  5. washthe filtrate was washed twice with water, once with NaHCO3
  6. dry with materialThe solution was dried (Na2SO4)
  7. concentrationconcentrated
  8. distillationThe product was purified by distillation at reduced pressure
  9. customcollecting the fraction bp 120-125° C./0.08 mm
  10. customto provide a colorless oil, mass

Sources & evidence

ORD record
ord-8afd15b7bfb14f129c8cf27e56ab6023
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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