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

HRID 1818677Notes

Reaction equation

HRID 1818677 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-78686bfe611b4c9d8c9118107acb3e2e
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

Loading…