Water → 5,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol

HRID 2118764Notes

Reaction equation

HRID 2118764 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]([OH:19])([CH2:15][C:16](O)=[O:17])[CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]([OH:19])([CH2:15][CH2:16][OH:17])[CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 201931955,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 201932595,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

15.5 g of 5,8-dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneacetic acid in 150 ml of tetrahydrofuran were added dropwise within 15 minutes to 3.32 g of lithium aluminum hydride in 150 ml of tetrahydrofuran. The reaction mixture was heated to reflux for 1 hour and then cooled. After the dropwise addition of 15 ml of ethyl acetate and 20 ml of water the suspension was filtered and the filtrate was concentrated. The product was purified by column chromatography (silica gel, chloroform/methanol 30:1). There was obtained 5,8-dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol, m.p. 121°-122°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. customThe product was purified by column chromatography (silica gel, chloroform/methanol 30:1)

Sources & evidence

ORD record
ord-e5c5f0ec6ca846a98812021bed316aab
Source dataset
uspto-grants-1987_07
Patent number
US04680310

Reaction notes

Loading…