5,6,7,8-Tetrahydro-1-naphthalenecarboxylic acid → (5,6,7,8-Tetrahydronaphthalen-1-yl)methanol

HRID 976046Notes

Reaction equation

HRID 976046 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:17](O)=[O:18])[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.OS([O-])(=O)=O.[K+]>CCOCC.C1COCC1>[OH:18][CH2:17][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 2396045,6,7,8-Tetrahydro-1-naphthalenecarboxylic acidHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15562329(5,6,7,8-Tetrahydronaphthalen-1-yl)methanolYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20 mL (0.019 mol) of 1.0M LiAlH4 in Et2O was cooled to -78° C. and treated dropwise with a solution of 3.42 g (0.019 mol) of 5,6,7,8-tetrahydro-1-naphthoic acid in 20 mL THF. The solution was allowed to warm to room temperature and stirred overnight. The solution was cooled to 0° C. and decomposed with 40 mL of a 0.43M solution of KHSO4. The mixture was filtered through Celite and washed with EtOAc. The organic phase was washed with 1N HCl and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 3.02 g (98% yield) of the product. The structure was confirmed by NMR spectroscopy.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with EtOAc
  4. washThe organic phase was washed with 1N HCl and saturated NaCl
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-37f286ecc82b455eaf25b80539d55465
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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