Vinyl ether → 2,3:4,5-Di(2-butenyl)tetrahydrofurfural

HRID 1399474Notes

Reaction equation

HRID 1399474 reaction equation
[CH:1]#[C:2][C:3]1C=CC(O)=C[CH:4]=1.C([O:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=C.[CH:21]([O:23]C=C)=C.C(N(CC)CC)C>C(OC(C)COC)(=O)C.CCCCCC.C(OCC)(=O)C>[CH2:1]1[CH:14]2[CH:15]3[C:16]([CH:21]=[O:23])([O:12][CH:13]2[CH2:4][CH:3]=[CH:2]1)[CH2:17][CH:18]=[CH:19][CH2:20]3

Participants

8

Reactant 4

HCID 8024Vinyl etherHCID 8471TriethylamineHCID 327584-EthynylphenolHCID 21363356[2-(Ethenyloxy)ethyl]cyclohexane

Product 1

HCID 313412,3:4,5-Di(2-butenyl)tetrahydrofurfural

Reagents, catalysts & solvents 3

HCID 7946Propylene glycol methyl ether acetateSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Poly(p-hydroxystyrene) (VP-2500, produced by Nippon Soda Co., Ltd.) (30 g) as a polyhydroxystyrene compound was dissolved in 120 g of PGMEA (propylene glycol monomethyl ether acetate). To this solution, 10.40 g of 2-cyclohexylethyl vinyl ether as a vinyl ether compound and 1.45 g of 2 mass % comphorsulfonic acid (PGMEA solution) were added thereto, and the mixture was stirred at room temperature for 2 hours. Furthermore, 1.05 g of 10 mass % triethylamine (PGMEA solution) was added and after stirring for a while, the reaction solution was transferred to a separating funnel containing 165 mL of ethyl acetate. The organic layer was washed with 200 mL of distilled water three times, and ethyl acetate was removed in an evaporator. The obtained reaction solution was added dropwise to 2 L of hexane, and the supernatant was removed. The obtained product was dissolved in 95 g of PGMEA, and the low-boiling-point solvent was removed under reduced pressure conditions to obtain 132.3 g of a PGMEA solution (28.3 mass %) of Polymer Compound (R-11).

Workup

  1. stirringafter stirring for a while
  2. customthe reaction solution was transferred to a separating funnel
  3. washThe organic layer was washed with 200 mL of distilled water three times, and ethyl acetate
  4. customwas removed in an evaporator
  5. customThe obtained reaction solution
  6. customthe supernatant was removed
  7. dissolutionThe obtained product was dissolved in 95 g of PGMEA
  8. customthe low-boiling-point solvent was removed under reduced pressure conditions

Sources & evidence

ORD record
ord-f0b2908ba0864ea383ad52c75bca5637
Source dataset
uspto-grants-2014_12
Patent number
US08906600B2

Reaction notes

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