Sodium → 2,6-Bis(trifluoromethyl)benzenemethanol

HRID 1720085Notes

Reaction equation

HRID 1720085 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]([F:28])([F:27])[C:13]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:14]=1[C:15](OC)=[O:16].[K].[Na]>C1(C)C=CC=CC=1>[F:11][C:12]([F:27])([F:28])[C:13]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[C:14]=1[CH2:15][OH:16]

Participants

6

Reactant 4

HCID 5360545SodiumHCID 5462222PotassiumHCID 21225700DiisobutylaluminumhydrideHCID 22420073Methyl 2,6-bis(trifluoromethyl)benzoate

Product 1

HCID 153464312,6-Bis(trifluoromethyl)benzenemethanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

58 ml of a 1.2M solution of diisobutylaluminium hydride (DIBAH) were added at 0° C. to a solution of 5.59 g of the product of Stage A and 60 ml of toluene. The temperature was allowed to return to 20° C. and the reaction mixture was stirred for 4 hours, then poured into a molar solution of potassium and sodium double tartrate and extracted with isopropyl ether. The aqueous phase was saturated with sodium chloride, followed by extraction with ethyl acetate, drying, filtering, rinsing and bringing to dryness to obtain after chromatography on silica (eluant: hexane-ethyl acetate (9-1)), 4.72 g of the desired product.

Workup

  1. customto return to 20° C.
  2. extractionextracted with isopropyl ether
  3. extractionfollowed by extraction with ethyl acetate
  4. customdrying
  5. filtrationfiltering
  6. washrinsing

Sources & evidence

ORD record
ord-85784df3dd1b437eb489df32cab2f0c6
Source dataset
uspto-grants-1996_04
Patent number
US05504112

Reaction notes

Loading…