Water → HCID 15588650, compound

HRID 2058000Notes

Reaction equation

HRID 2058000 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:13]([F:14])=[C:12]([F:15])[C:11]([F:16])=[C:10]([F:17])[C:9]=1[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21](OC)=[O:22].O>O1CCCC1>[F:7][C:8]1[C:13]([F:14])=[C:12]([F:15])[C:11]([F:16])=[C:10]([F:17])[C:9]=1[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[CH2:21][OH:22]

Participants

5

Reactant 3

HCID 962WaterHCID 13216677HCID 13216677, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15588650HCID 15588650, compoundYield 121.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of 0.5 g of lithium aluminum hydride in 50 ml of dry tetrahydrofuran, cooled to -78°, was added dropwise methyl 3-(2,3,4,5,6-pentafluorophenyl)benzoate (2.6 g, 0.009 mole) in 50 ml of dry tetrahydrofuran. Upon complete addition, the reaction mixture was stirred while warming to room temperature. A solution of 10% water in tetrahydrofuran was then added dropwise to the reaction mixture to destroy excess lithium aluminum hydride. An additional 50 ml of water was then added, and the liquid phases separated. The aqueous layer was washed with two 50 ml portions of diethyl ether. The ether washes were combined with the organic layer from the reaction mixture and dried. The mixture was filtered and the filtrate evaporated under reduced pressure to give 3-(2,3,4,5,6-pentafluorophenyl)benzyl alcohol (3.0 g) as an oil, which solidified on standing. The ir spectrum was consistent with the proposed structure.

Workup

  1. temperaturecooled to -78°
  2. additionUpon complete addition
  3. customto destroy excess lithium aluminum hydride
  4. additionAn additional 50 ml of water was then added
  5. customthe liquid phases separated
  6. washThe aqueous layer was washed with two 50 ml portions of diethyl ether
  7. customdried
  8. filtrationThe mixture was filtered
  9. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-586e2cc74b2c4335ab2946dba8a486a3
Source dataset
uspto-grants-1980_07
Patent number
US04214004

Reaction notes

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