Hydrochloric Acid → (5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

HRID 963704Notes

Reaction equation

HRID 963704 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C@H:13]([C:19](OC)=[O:20])[CH2:14]2.Cl>O1CCCC1>[CH3:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([CH2:19][OH:20])[CH2:14]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 22866788(S)-methyl (5-methoxy-1,2,3,4-tetrahydro-2-naphthyl)formate

Product 1

HCID 53744579(5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanolYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of lithium aluminum hydride (0.28 g) in dry tetrahydrofuran (THF) (5 ml) was added dropwise a solution of (S)-methyl [5-methoxy-1,2,3,4-tetrahydro-2-naphthyl]formate (1.65 g) in THF (7 ml) at -60° C. under nitrogen. After 1 hour, a mixture of 1N hydrochloric acid solution (5 ml) and THF (5 ml) was added dropwise to the reaction mixture at -60° C. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with 1N hydrochloric acid solution, sodium hydrogencarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo to give (5-methoxy-1,2,3,4-tetrahydro-2-naphthyl)methanol as a white powder (1.23 g). [α]D30 =71.98° (C=1.26, CH2Cl2)

Workup

  1. additionwas added dropwise to the reaction mixture at -60° C
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with 1N hydrochloric acid solution, sodium hydrogencarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-35b8f90b2f4f40f8b1d1080abd825198
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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