Triphenylacetic acid → 2,2,2-Triphenylethanol

HRID 908537Notes

Reaction equation

HRID 908537 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](O)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:23]1([C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:14][OH:15])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 68992Triphenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2438942,2,2-TriphenylethanolYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LAH (3.9 g, 0.104 mol) in dry THF (200 mL) was stirred at 0° C. for 20 min. A solution of 2,2,2-triphenylacetic acid (10 g, 0.034 mol) in dry THF (50 mL) was added in a drop-wise manner. The reaction mixture was stirred at RT overnight. Excess LAH was quenched with 1.5 N HCl and the reaction mixture was further stirred for 2 h at RT. The reaction mixture was filtered through celite, washed with ethyl acetate and the filtrate was concentrated under vacuum. The crude product was purified by column chromatography on silica gel (4% ethyl acetate in pet. ether) to give the title compound (4.6 g, 48%). TLC: Pet. ether/EtOAc, 7:3, Rf=0.2

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. customExcess LAH was quenched with 1.5 N HCl
  3. stirringthe reaction mixture was further stirred for 2 h at RT
  4. filtrationThe reaction mixture was filtered through celite
  5. washwashed with ethyl acetate
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe crude product was purified by column chromatography on silica gel (4% ethyl acetate in pet. ether)

Sources & evidence

ORD record
ord-c1df37c68d9340a9b02840c5cc43254e
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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