Hydrochloric Acid → 2-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanol

HRID 963691Notes

Reaction equation

HRID 963691 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][C:14](OCC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14][OH:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10538520Ethyl 2-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 106083702-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanolYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of ethyl (5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)acetate (1.02 g) and lithium aluminum hydride (0.20 g) in tetrahydrofuran (15 ml) was stirred at 0° C. for 2.5 hours. The solution was poured into cold 1N-hydrochloric acid, then the resulting mixture was filtered through the celite, and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and evaporated in vacuo to afford 2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanol as a colorless oil (0.85 g).

Workup

  1. filtrationthe resulting mixture was filtered through the celite
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-53d3df0b49da466c85edf482b943f878
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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