Ethyl vinyl ether → HCID 10366771, compound

HRID 1640058Notes

Reaction equation

HRID 1640058 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH:27]([O:29][CH2:30][CH3:31])=[CH2:28].C(=O)([O-])O.[Na+]>O.O1CCCC1>[CH2:27]([O:29][CH:30]([O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:31])[CH3:28]

Participants

7

Reactant 4

HCID 8023Ethyl vinyl etherHCID 90073-MethoxyphenolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 10366771HCID 10366771, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2600 mL of tetrahydrofuran and 650.4 g (5.24 mol) of 3-methoxyphenol were added to a 15 L four-necked round bottom flask under a nitrogen atmosphere. Subsequently 65.8 g (0.26 mol) of pyridinium p-toluenesulfonate was added to this tetrahydrofuran solution and stirring was started. This mixture was cooled in a temperature-controlled bath set to 8° C. and 760.1 g (10.54 mol) of ethyl vinyl ether was added dropwise to the reaction mixture for about 1.5 hours. The reaction mixture was stirred at the same temperature for 2.7 hours and then the temperature of the temperature-controlled bath was set to 15° C. It was further stirred for about 2 hours from a time point when the inner temperature exceeded 14° C. The temperature of the temperature-controlled bath was set to 8° C., and at a time point when the inner temperature reached almost 10° C., 715.2 g of 8% sodium hydrogen carbonate aqueous solution [prepared by dissolving 57.2 g of sodium hydrogen carbonate in 658 mL of water] was added dropwise to the reaction mixture over 10 minutes. The reaction mixture was transferred to a 20 L separatory funnel and added with 1040 mL of water and added and extracted with 4550 mL of toluene and the organic layer was washed with 1300 mL and 650 mL of water twice. The obtained organic layer was concentrated in vacuo at a bath temperature of 40° C. and a pale yellow oil containing the title compound was obtained.

Workup

  1. temperatureThis mixture was cooled in a temperature-controlled bath
  2. customset to 8° C.
  3. stirringThe reaction mixture was stirred at the same temperature for 2.7 hours
  4. customwas set to 15° C
  5. stirringIt was further stirred for about 2 hours from a time point when the inner temperature
  6. customexceeded 14° C
  7. customwas set to 8° C.
  8. customreached almost 10° C.
  9. customThe reaction mixture was transferred to a 20 L separatory funnel
  10. additionadded
  11. extractionextracted with 4550 mL of toluene
  12. washthe organic layer was washed with 1300 mL and 650 mL of water twice
  13. concentrationThe obtained organic layer was concentrated in vacuo at a bath temperature of 40° C.
  14. additiona pale yellow oil containing the title compound
  15. customwas obtained

Sources & evidence

ORD record
ord-1416e9d9a6724290b2e45123861f1fd1
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

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