Ethyl Acrylate → HCID 18518690, compound

HRID 1385986Notes

Reaction equation

HRID 1385986 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-de8c9fd6a6484ea3b2c1623ac63a91a4
Source dataset
uspto-grants-2001_07
Patent number
US06265397B1

Reaction notes

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