Water → 3-(Naphthalen-1-yl)propan-1-ol

HRID 381792Notes

Reaction equation

HRID 381792 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH2:17][CH2:18][C:19](OCC)=[O:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.O>CCOCC>[C:7]1([CH2:17][CH2:18][CH2:19][OH:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10966256Ethyl 3-(1-naphthyl)propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 147115183-(Naphthalen-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of LiAlH4 (1.91 g, 50.4 mmol) in anhydrous ether (50 mL) was added dropwise a solution of 8 (11.5 g, 50.4 mmol) in ether (50 mL) over 30 minutes at 0° C. under argon and then the mixture was stirred at room temperature (overnight). The reaction mixture was cooled to 0° C. and quenched by slow (30 minutes addition of H2O (7.2 mL, 0.4 mol), then the mixture was stirred at 0° C. (1 h). Solid was removed by filtration washed with ether, then the combined ether solution was dried (Na2SO4) and taken to dryness, yielding 9 as an oil70 (9.36 g, 100%). 1H NMR (CDCl3) δ 8.08 (1H, dd, J=2.4, 7.4 Hz), 7.88 (1H, m), 7.74 (1H, d, J=7.6 Hz), 7.34˜7.57 (4H, m), 3.76 (2H, t, J=6.4 Hz), 3.20 (2H, t, J=7.5 Hz), 2.05 (2H, m), 1.75 (1H, brs).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched by slow (
  3. stirringthe mixture was stirred at 0° C. (1 h)
  4. customSolid was removed by filtration
  5. washwashed with ether
  6. dry with materialthe combined ether solution was dried (Na2SO4)
  7. customyielding 9 as an oil70 (9.36 g, 100%)

Sources & evidence

ORD record
ord-06593753513646d6a900049ea6813757
Source dataset
uspto-grants-2001_10
Patent number
US06307090B1

Reaction notes

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