Water → HCID 23108397, compound

HRID 1270608Notes

Reaction equation

HRID 1270608 reaction equation
[OH:1][C:2]1([C:12]([F:21])([F:20])[C:13](O)([OH:18])[C:14]([F:17])([F:16])[F:15])[CH2:7][CH2:6][CH:5]([C:8](OC)=[O:9])[CH2:4][CH2:3]1.O>C1(C)C=CC=CC=1>[OH:1][C:2]1([C:12]([F:20])([F:21])[CH:13]([OH:18])[C:14]([F:15])([F:16])[F:17])[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 23108407HCID 23108407, compound

Product 1

HCID 23108397HCID 23108397, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 300 ml of toluene was dissolved 30.0 g of methyl 4-hydroxy-4-(2,2-dihydroxy-1,1,3,3,3-pentafluoropropyl)-cyclohexanecarboxylate obtained in <6-1>. The solution was stirred and heated under reflux while the water formed was continuously removed. Under nitrogen atmosphere and with stirring, this solution was added dropwise to a solution of 5.0 g lithium aluminum hydride in 100 ml tetrahydrofuran. The mixture was stirred at 5° C. for one hour and then at room temperature for 18 hours. The reaction mixture was combined with 500 ml of 10% hydrochloric acid and extracted with ethyl acetate. Through conventional work-up including washing, drying and concentration, a crude product was obtained. Recrystallization from n-hexane gave 20.8 g (yield 80%) of the target compound.

Workup

  1. customobtained in <6-1>
  2. temperatureheated
  3. customformed
  4. customwas continuously removed
  5. stirringUnder nitrogen atmosphere and with stirring
  6. additionthis solution was added dropwise to a solution of 5.0 g lithium aluminum hydride in 100 ml tetrahydrofuran
  7. stirringThe mixture was stirred at 5° C. for one hour
  8. extractionextracted with ethyl acetate
  9. washThrough conventional work-up including washing
  10. customdrying
  11. concentrationconcentration
  12. customa crude product was obtained
  13. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-58259768fedc4a3686782561bbfadbda
Source dataset
uspto-grants-2007_04
Patent number
US07202318B2

Reaction notes

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