Ethyl Acrylate → HCID 18518690, compound

HRID 1369016Notes

Reaction equation

HRID 1369016 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[OH:11].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>C(O)C>[Cl:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[O:11][CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 874592-Chloro-4-methoxyphenolHCID 5360545Sodium2×

Product 1

HCID 18518690HCID 18518690, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

Sodium (0.055 g; 2.4 mmol) and ethanol (1.5 mL) was added to a melt of 2-chloro-4-methoxyphenol (5.20 g; 32.8 mmol). When all the sodium was dissolved, ethyl acrylate (4.1 g; 41 mmol) was added and the mixture was heated at 105° C. for 7 days. The mixture was then cooled to RT and partitioned between ether and water. The mixture was made acidic with HCl (2M; aq.) and extracted with ether three times. The combined organic layer was washed with NaOH (2M; aq), dried (CaCl2) and evaporated. The crude product (2.7 g) was purified using preparative RPLC (CH3CN:0.1M ammonium acetate (60:40)). Yield 1.90 g (22%).

Workup

  1. temperatureThe mixture was then cooled to RT
  2. custompartitioned between ether and water
  3. extractionextracted with ether three times
  4. washThe combined organic layer was washed with NaOH (2M; aq)
  5. dry with materialdried (CaCl2)
  6. customevaporated
  7. customThe crude product (2.7 g) was purified

Sources & evidence

ORD record
ord-cc67a08b969d41e4962d468f7fb151ac
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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