Water → (7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

HRID 1762579Notes

Reaction equation

HRID 1762579 reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH3:17][O:16][C:10]1[CH:9]=[C:8]2[C:13]([CH2:14][CH2:15][CH:6]([CH2:4][OH:3])[CH2:7]2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54368774Ethyl 7-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate

Product 1

HCID 10797825(7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 23.43 g (100 mmol) of 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester in 160 ml of absolute tetrahydrofuran is added dropwise, over a period of 30 minutes, while stirring at room temperature, to a suspension of 3.79 g (100 mmol) of lithium aluminium hydride in 160 ml of absolute diethyl ether. After stirring at room temperature for 1 hour, 3.8 ml of water, 3.8 ml of sodium hydroxide solution (15%) and 11.4 ml of water are added to the reaction mixture. The resulting precipitate is filtered off with suction and the filtrate is concentrated to dryness by evaporation in vacuo. The oily residue is dissolved in diethyl ether, washed with water, dried with sodium sulphate and concentrated to dryness by evaporation. 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-methanol is obtained in the form of a yellow oil.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. concentrationthe filtrate is concentrated to dryness by evaporation in vacuo
  3. dissolutionThe oily residue is dissolved in diethyl ether
  4. washwashed with water
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-d7618f7896ed4363b04cd1d926e25020
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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