Tetrahydrofuran → 4,4'-(Perfluoroisopropylidene)dicyclohexanol dimethacrylate

HRID 2232663Notes

Reaction equation

HRID 2232663 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([CH:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1)([CH:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[O:31]1CCCC1.[C:36](Cl)(=[O:40])[C:37]([CH3:39])=[CH2:38]>O>[C:36]([OH:40])(=[O:14])[C:37]([CH3:39])=[CH2:38].[C:36]([OH:40])(=[O:31])[C:37]([CH3:39])=[CH2:38].[F:1][C:2]([F:22])([F:23])[C:3]([CH:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1)([CH:8]1[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]1)[C:4]([F:5])([F:7])[F:6]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 27822244-[1,1,1,3,3,3-Hexafluoro-2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol

Product 1

HCID 867425564,4'-(Perfluoroisopropylidene)dicyclohexanol dimethacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a reaction vessel equipped with a stirrer, thermometer and dropping funnel were placed 0.3 mole (104.4 g) of 4,4'-(perfluoroisopropylidene)dicyclohexanol, 1 mole (101.2 g) of triethylamine and 700 ml of tetrahydrofuran. To the mixture was added dropwise 1 mole (104.5 g) of methacryloyl chloride while cooling the mixture with ice. The mixture was maintained at a temperature below 20° C. for 8 hours with stirring. The reaction mixture was poured into a large excess amount of water and the resulting precipitates were recovered and washed with methanol to obtain 69 g of 4,4'-(perfluoroisopropylidene)dicyclohexanol dimethacrylate in the form of white solid.

Workup

  1. customInto a reaction vessel equipped with a stirrer
  2. temperaturewhile cooling the mixture with ice
  3. temperatureThe mixture was maintained at a temperature below 20° C. for 8 hours
  4. customthe resulting precipitates
  5. customwere recovered
  6. washwashed with methanol

Sources & evidence

ORD record
ord-c5ad444026bb4f39964f67c287ddfc7b
Source dataset
uspto-grants-1988_11
Patent number
US04788327

Reaction notes

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