Sulfuric Acid → 4,4,4-Trifluoro-3-methylbut-2-en-1-ol

HRID 888337

Reaction equation

HRID 888337 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([CH3:10])=[CH:4][C:5](OCC)=[O:6].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)O>O1CCCC1>[F:1][C:2]([F:12])([F:11])[C:3]([CH3:10])=[CH:4][CH2:5][OH:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 342470Ethyl 4,4,4-trifluoro-3-methyl-2-butenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 540431804,4,4-Trifluoro-3-methylbut-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.5 g of ethyl 4,4,4-trifluoro-3-methyl-2-butenoate in 50 ml of tetrahydrofuran was added dropwise 48 ml of diisobutylaluminum hydride (1.02M solution in hexane) under ice-cooling. The reaction mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added diluted sulfuric acid and then extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain crude 4,4,4-trifluoro-3-methyl-2-buten-1-ol.

Workup

  1. temperaturecooling
  2. extractionextracted with t-butyl methyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5cd26017bd1b418980424a307e553aab
Source dataset
uspto-grants-2012_08
Patent number
US08247595B2

Linked notes

Loading…