4-Hydroxybenzaldehyde → HCID 86718846, compound

HRID 2283149Notes

Reaction equation

HRID 2283149 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]([F:41])([F:40])[C:18]([F:39])([F:38])[C:19]([F:37])([F:36])[O:20][C:21]([F:35])([C:26]([F:34])([F:33])[O:27][C:28]([F:32])=[C:29]([F:31])[F:30])[C:22]([F:25])([F:24])[F:23].C(C1C=CC=C(OC(F)(F)C(F)OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C=1)#C>O1CCCC1>[F:31][C:29]([F:30])([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH:28]([F:32])[O:27][C:26]([F:33])([F:34])[C:21]([F:35])([O:20][C:19]([F:36])([F:37])[C:18]([F:38])([F:39])[C:17]([F:16])([F:40])[F:41])[C:22]([F:25])([F:24])[F:23]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 1026621,1,1,2,3,3-Hexafluoro-2-(heptafluoropropoxy)-3-((trifluorovinyl)oxy)propaneHCID 86718847HCID 86718847, compound

Product 1

HCID 86718846HCID 86718846, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the dry box, tetrahydrofuran (25 mL) and 4-hydroxybenzaldehyde (0.61 g, 0.005 mol) were added to a round bottom flask equipped with a stirrer. Potassium carbonate (0.175 g, 0.00126 mol) was then added to the flask. 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 (3.24 g, 0.0075 mol) was then added via the addition funnel and the reaction was placed in an oil bath and heated to a gentle reflux for two hours. The content was analyzed by proton NMR and shown to be 1-ethynyl-3-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)benzene.

Workup

  1. customequipped with a stirrer
  2. customthe reaction was placed in an oil bath
  3. temperatureheated to
  4. temperaturea gentle reflux for two hours

Sources & evidence

ORD record
ord-1623176b2610453a86da013f7604650c
Source dataset
uspto-grants-2015_09
Patent number
US09145356B2

Reaction notes

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