6-(Decyloxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid → HCID 23297274, compound

HRID 1953360Notes

Reaction equation

HRID 1953360 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH:23]([C:28](O)=[O:29])[CH2:22][CH2:21]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CCOCC>[CH2:7]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH:23]([CH2:28][OH:29])[CH2:22][CH2:21]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 189601216-(Decyloxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 23297274HCID 23297274, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.34 g (8.95 mmol) of lithium aluminum hydride was added to 40 ml of ether. To this mixture was slowly added 2.54 g (7.65 mmol) of the 6-decyloxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid obtained in the first stage of Example 1. After the resulting mixture was stirred at room temperature for 30 minutes, it was heated under reflux for 6 hours. After cooling, the reaction mixture was caused to undergo hydrolysis and extraction with ether. The organic phase was concentrated and by purifying the concentrate using column chromatography there was obtained 2.31 g (7.26 mmol) of 6-decyloxy-1,2,3,4-tetrahydro-2-hydroxymethylnaphthalene as a white solid.

Workup

  1. customobtained in the first stage of Example 1
  2. temperatureit was heated
  3. temperatureunder reflux for 6 hours
  4. temperatureAfter cooling
  5. concentrationThe organic phase was concentrated
  6. customby purifying the concentrate

Sources & evidence

ORD record
ord-877250b1befc4293a5f6a8fe3ca5e3d9
Source dataset
uspto-grants-2000_09
Patent number
US06117359

Reaction notes

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