Sodium Sulfate → (1,2,3,4-Tetrahydronaphthalen-2-yl)methanol

HRID 1732105Notes

Reaction equation

HRID 1732105 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11](O)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:12][CH2:11][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 245056(1,2,3,4-Tetrahydronaphthalen-2-yl)methanolYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.0 g (0.028 mol) 1,2,3,4-tetrahydro-2-naphthoic acid in 30 ml of dry tetrahydrofuran, 1.1 g (0.029 mol) lithium aluminum hydride was added over a period of one half hour. After the addition was completed, the mixture was stirred at room temperature for a period of 2 hours. It was then cooled on ice, and was carefully decomposed with a minimum amount of saturated Na2SO4 solution. The reaction mixture was filtered and washed with ether. The organic layer was combined and extracted with water. Concentration of the dried organic layer yielded 4.4 g of crude product.

Workup

  1. additionAfter the addition
  2. temperatureIt was then cooled on ice
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ether
  5. extractionextracted with water

Sources & evidence

ORD record
ord-56eee9ffdd364ed0854dc075958fff39
Source dataset
uspto-grants-1986_11
Patent number
US04625034

Reaction notes

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