3,3,3-Triphenylpropionic Acid → 3,3,3-Triphenylpropan-1-ol

HRID 1713385Notes

Reaction equation

HRID 1713385 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C:15](O)=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:24]1([C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14][CH2:15][OH:16])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 1366963,3,3-Triphenylpropionic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2986573,3,3-Triphenylpropan-1-olYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a magnetically stirred suspension of LAH (8.3 g, 0.219 mol) in dry THF (50 mL) was added a solution of 3,3,3-triphenylpropionic acid (9.5 g, 0.0314 mol) over a period of 30 min at 0° C. The reaction mixture was allowed to stir at RT for 14 h. The reaction mixture was cooled and excess LAH was quenched with 20% NaOH solution (50 mL). The reaction mixture was passed through celite, washed with THF and the filtrate was concentrated under vacuum. The residue was washed with pet ether and dried which gave the title compound (8 g, >85%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customexcess LAH was quenched with 20% NaOH solution (50 mL)
  3. washwashed with THF
  4. concentrationthe filtrate was concentrated under vacuum
  5. washThe residue was washed with pet ether
  6. customdried which

Sources & evidence

ORD record
ord-ec5a2a35056b4fcd98042c6adb0aed28
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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