Water → {[(3,3,3-Trifluoroprop-1-en-1-yl)oxy]methyl}benzene

HRID 1985028Notes

Reaction equation

HRID 1985028 reaction equation
O.S(=O)(=O)(O)O.[F:7][C:8]([F:13])([F:12])[CH2:9][CH:10]=[O:11].[CH2:14]([O:21]C=CC(F)(F)F)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[F:28][C:29]([F:49])([F:48])[CH2:30][CH:31]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:33]([O:32][CH:31]=[CH:30][C:29]([F:28])([F:49])[F:48])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[F:28][C:29]([F:48])([F:49])[CH2:30][CH:31]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[F:7][C:8]([F:13])([F:12])[CH2:9][CH:10]=[O:11]

Participants

9

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 680283,3,3-TrifluoropropanalHCID 53395476{[(3,3,3-Trifluoroprop-1-en-1-yl)oxy]methyl}benzene2×HCID 668097261,1′-[(3,3,3-Trifluoropropylidene)bis(oxymethylene)]bis[benzene]

Product 4

HCID 244Benzyl AlcoholYield 2.5%HCID 680283,3,3-TrifluoropropanalHCID 53395476{[(3,3,3-Trifluoroprop-1-en-1-yl)oxy]methyl}benzeneYield 4.7%HCID 668097261,1′-[(3,3,3-Trifluoropropylidene)bis(oxymethylene)]bis[benzene]Yield 0.1%

Conditions

Temperature
100 °C

Procedure

A mixture (composition: 2.5% benzyl alcohol, 92.7% (1E) 1-benzyloxy-3,3,3-trifluoropropene, 4.7% (1Z) 1-benzyloxy-3,3,3-trifluoropropene and 0.1% 1,1,1-trifluoro-3,3-dibenzyloxypropane) was prepared in the same way as in Example 3. Then, 34 g of the prepared mixture was filled into a 100-ml three-neck glass flask with a magnetic stirrer, a thermometer and a reflux condenser, followed by adding thereto 1.5 g (0.08 mol) water and 0.67 g (0.007 mol) 98% sulfuric acid and stirring the mixture under heating at 100° C. for 2 hours. The resulting reaction solution was analyzed by gas chromatography and found to contain 66.2% target 3,3,3-trifluoropropionaldehyde, 1% (1E) 1-benzyloxy-3,3,3-trifluoropropene, 0.4% (1Z) 1-benzyloxy-3,3,3-trifluoropropene and 1.4% 1,1,1-trifluoro-3,3-dibenzyloxypropane. After replacing the reflux condenser with a distillation column and a receiver flask, the reaction solution was subjected to distillation to obtain the target 3,3,3-trifluoropropionaldehyde as a distillate fraction of boiling point 55 to 57° C. (yield amount: 10 g, yield rate: 53.9%, purity: 99%).

Workup

  1. additionby adding
  2. customThe resulting reaction solution
  3. distillationwith a distillation column and a receiver flask
  4. distillationthe reaction solution was subjected to distillation

Sources & evidence

ORD record
ord-210e41d1b3ce4ce5a40f6d8bcc69d809
Source dataset
uspto-grants-2009_06
Patent number
US07544844B2

Reaction notes

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