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

HRID 1424708Notes

Reaction equation

HRID 1424708 reaction equation
[CH:1]1([C:11](O)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>O1CCCC1>[CH:1]1([CH2:11][OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 125981461,2,3,4-Tetrahydro-1-naphthoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11062704(1,2,3,4-Tetrahydronaphthalen-1-yl)methanolYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (1.10 mmol) of 1,2,3,4-tetrahydro-naphthalen-1-carboxylic acid compound was dissolved in 9 mL of tetrahydrofuran, and then 129 mg (3.30 mmol) of lithium aluminum hydride was added at 0° C. and stirred at room temperature for 1 hour. Water was slowly added to quench the reaction, and when a gel was formed by adding ethyl acetate, the celite was filtered. Then, the residue was dissolved again in 20 mL of ethyl acetate and the organic layer was washed with distilled water three times. The organic layer was dried with anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 180 mg of colorless oil (yield: 97%).

Workup

  1. customto quench
  2. customthe reaction, and when a gel
  3. customwas formed
  4. filtrationthe celite was filtered
  5. dissolutionThen, the residue was dissolved again in 20 mL of ethyl acetate
  6. washthe organic layer was washed with distilled water three times
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd5b3c7e23494a7387d9310c75d43ddc
Source dataset
uspto-grants-2015_01
Patent number
US08927760B2

Reaction notes

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