Diisobutylaluminumhydride → [3-Methyl-4'-(trifluoromethyl)biphenyl-4-yl]methanol

HRID 1669239Notes

Reaction equation

HRID 1669239 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][C:6]=1[CH3:21])=O.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:21][C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]=1[CH2:3][OH:2]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 673420563-Methyl-4'-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 22280004[3-Methyl-4'-(trifluoromethyl)biphenyl-4-yl]methanolYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-4′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (1.993 g, 6.773 mmol) in CH2Cl2 (34 mL) at 0° C. is treated with 1.0 M diisobutylaluminum hydride in toluene (DIBAL, 14.3 mL) dropwise over 3 min. time and stirred for 3.5 h. The reaction mixture is quenched with MeOH (5.0 mL), treated with 1M tartaric acid (50 mL), and stirred overnight. The organic layer is separated. The aqueous layer is extracted with CH2Cl2 (1×50 mL). Combined organic extracts are dried over MgSO4, filtered, and conc. to provide (3-methyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (1.616 g, 90%) as a white solid.

Workup

  1. customThe reaction mixture is quenched with MeOH (5.0 mL)
  2. additiontreated with 1M tartaric acid (50 mL)
  3. stirringstirred overnight
  4. customThe organic layer is separated
  5. extractionThe aqueous layer is extracted with CH2Cl2 (1×50 mL)
  6. dry with materialCombined organic extracts are dried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b9b42994a2c3425a92ba7ec7fdff5e05
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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