2,2-Dimethyl-4-phenylbutanoic acid → HCID 59141048, compound

HRID 530499Notes

Reaction equation

HRID 530499 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([CH3:20])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9](O)=[O:10]>CCOCC>[CH3:7][C:8]([CH3:20])([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 124737192,2-Dimethyl-4-phenylbutanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 59141048HCID 59141048, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C., under nitrogen atmosphere, to a stirring mixture of LiAlH4 (0.49 g, 12.8 mmol) in dry Et2O (25 mL), 2,2-dimethyl-4-phenyl-butanoic acid (0.62 g, 3.22 mmol) dissolved in Et2O (10 mL) was added dropwise. The mixture was left at rt for 4 h, then quenched at 0° C. by slowly adding H2O (0.5 mL) followed by 3M KOH solution (0.5 mL) and H2O (1.64 mL). The mixture was stirred for 1 h at 0° C., then the crude was filtered and the organic phase dried over Na2SO4. The organic solution was concentrated to dryness affording the title compound (0.540 g, 94%) as pale yellow transparent oil. 1H NMR (CDCl3): δ 0.96 (s, 6H), 1.55-1.64 (m, 2H), 2.58-2.65 (m, 2H) 3.41 (s, 2H), 7.17-7.33 (m, 5H).

Workup

  1. additionwas added dropwise
  2. customquenched at 0° C. by slowly adding H2O (0.5 mL)
  3. filtrationthe crude was filtered
  4. dry with materialthe organic phase dried over Na2SO4
  5. concentrationThe organic solution was concentrated to dryness

Sources & evidence

ORD record
ord-b2e2e579885c4463adb347b9bb4249a7
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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