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Water → ADONA

HRID 473391
Notes
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Reaction equation

HRID 473391 reaction equation
[OH2:1].[C-]#N.[K+].[C:5](=[C:8]([O:10][C:11]([C:14]([C:17]([O:20][C:21]([F:24])([F:23])[F:22])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])[F:9])([F:7])[F:6].OS(O)(=O)=O.COCC[O:34][CH3:35]>>[C:35]([C:5]([CH:8]([O:10][C:11]([C:14]([C:17]([O:20][C:21]([F:22])([F:23])[F:24])([F:18])[F:19])([F:16])[F:15])([F:13])[F:12])[F:9])([F:7])[F:6])([OH:34])=[O:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 80711,2-DimethoxyethaneHCID 9032Potassium CyanideHCID 22613616Hexafluoro-1-trifluoromethoxy-3-trifluorovinyloxypropane

Product 1

HCID 52915299ADONAYield 89%

Conditions

Temperature
50 °C

Procedure

A mixture consisting of 120 ml H2O, 250 ml ethyleneglycol dimethylether and 26.3 g KCN was heated to 50° C. 110 g MV31 (CF2═CF—O—(CF2)3—O—CF3) were added to the mixture over a period of 35 min. During the addition of MV31 the temperature of the reaction mixture rose to 57° C. The reaction mixture was cooled down to 25° C. before 55 ml concentrated H2SO4 were added. The bottom phase was collected and washed with water. Afterwards, the organic phase was mixed with the same volume of conc. H2SO4 and agitated for 1 h at room temperature. Distillation from the reaction mixture yielded HOOC—CF2—CHF—O—(CF2)3—O—CF3 (overall yield 89%).

Workup

  1. additionDuring the addition of MV31 the temperature of the reaction mixture
  2. customrose to 57° C
  3. additionwere added
  4. customThe bottom phase was collected
  5. washwashed with water
  6. additionAfterwards, the organic phase was mixed with the same volume of conc. H2SO4
  7. distillationDistillation from the reaction mixture

Sources & evidence

ORD record
ord-9410b5a3d5b549b1b2dbe452f07e96d2
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633328B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes