Water → 4-Ethynylphenol

HRID 1416807Notes

Reaction equation

HRID 1416807 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[CH2:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC=C)C.O>O1CCOCC1>[CH:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962Water3×HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 624534-Vinylphenol

Product 1

HCID 327584-Ethynylphenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Into a 500 ml four-necked flask purged with nitrogen were charged 25 g of poly (p-vinylphenol) ["VP-5000" manufactured by Nippon Soda K.K.] having a weight average molecular weight (Mw) of 8400 and a dispersion degree (Mw/Mn) of 1.19 (208 mmol as p-vinylphenol unit) and 0.024 g (0.125 mmol) of p-toluenesulfonic acid, and they were dissolved in 250 g of 1,4-dioxane. To this solution was added dropwise 9.0 g (125 mmol) of ethylvinyl ether, and then reaction was carried out for 5 hours at 25° C. This reaction solution was added dropwise into 1500 ml of ion-exchanged water, then separated by filtration to obtain a white wet cake. This wet cake was dissolved again in 200 g of 1,4-dioxane, and the resulting solution was added dropwise into 1500 ml of ion-exchanged water. The resulting mixture was separated by filtration. The wet cake thus obtained was washed by being stirred with 600 g of ion-exchanged water, followed by being filtered to obtain a wet cake. The washing operation with this ion-exchanged water was further repeated twice. The resulting white wet cake was dried under reduced pressure to obtain a resin in which the hydroxyl group of poly (p-vinylphenol) was partially 1-ethoxyethyl etherized. This resin was analyzed by 1H-NMR to find that 40% of the hydroxyl group was protected by a 1-ethoxylethyl group. This resin has a weight average molecular weight of 12300 and a dispersion degree of 1.23.

Workup

  1. customInto a 500 ml four-necked flask purged with nitrogen
  2. additionwere charged 25 g of poly (p-vinylphenol) ["VP-5000" manufactured by Nippon Soda K.K.]
  3. customreaction
  4. customseparated by filtration
  5. customto obtain a white wet cake
  6. customThe resulting mixture was separated by filtration
  7. customThe wet cake thus obtained
  8. washwas washed
  9. filtrationby being filtered
  10. customto obtain a wet cake
  11. customThe resulting white wet cake was dried under reduced pressure

Sources & evidence

ORD record
ord-fb46830f5ac3458a92407902d695da49
Source dataset
uspto-grants-1999_06
Patent number
US05916728

Reaction notes

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