Methylparaben → HCID 86718849, compound

HRID 2283151Notes

Reaction equation

HRID 2283151 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:43])([F:42])[C:20]([F:41])([F:40])[C:21]([F:39])([F:38])[O:22][C:23]([F:37])([C:28]([F:36])([F:35])[O:29][C:30]([F:34])=[C:31]([F:33])[F:32])[C:24]([F:27])([F:26])[F:25]>C1COCC1>[F:33][C:31]([F:32])([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH:30]([F:34])[O:29][C:28]([F:35])([F:36])[C:23]([F:37])([O:22][C:21]([F:38])([F:39])[C:20]([F:40])([F:41])[C:19]([F:18])([F:42])[F:43])[C:24]([F:27])([F:26])[F:25]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 1026621,1,1,2,3,3-Hexafluoro-2-(heptafluoropropoxy)-3-((trifluorovinyl)oxy)propane

Product 1

HCID 86718849HCID 86718849, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the dry box, THF (500 mL) and methyl 4-hydroxybenzoate (26.6 g, 0.175 mol) were added to an oven dry RB flask equipped with a stirrer, Potassium carbonate (12.00 g, 0.087 mol) was then added. 1,1,1,2,2,3,3-Heptafluoro-3-(1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluorovinyloxy)propan-2-yloxy)propane (94.5 g, 0.219 mol) was then added via the addition funnel and the reaction allowed to stir at room temperature. The reaction mixture was heated to a gentle reflux, oil temperature about 80° C., under nitrogen overnight. An aliquot was withdrawn and concentrated under vacuum and analyzed via proton NMR that showed the complete conversion to the desired material. The cooled reaction mixture was then filtered through silica gel and then concentrated at reduced pressure, resulting in 101.52 g (99.33%) yield of the desired material.

Workup

  1. customdry RB flask
  2. customequipped with a stirrer
  3. temperatureThe reaction mixture was heated to a gentle reflux, oil temperature about 80° C., under nitrogen overnight
  4. customAn aliquot was withdrawn
  5. concentrationconcentrated under vacuum
  6. customThe cooled reaction mixture
  7. filtrationwas then filtered through silica gel
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-d1d77d59a0744a7a9ac60e2c594ed8f5
Source dataset
uspto-grants-2015_09
Patent number
US09145356B2

Reaction notes

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