Hydrochloric Acid → 2,2-Dibutyl-5-hydroxy-1,2,3,4-tetrahydro-1-naphthol

HRID 727811Notes

Reaction equation

HRID 727811 reaction equation
[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(OCC)C>[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[CH:6]1[OH:16])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10659962HCID 10659962, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 105166192,2-Dibutyl-5-hydroxy-1,2,3,4-tetrahydro-1-naphtholYield 93.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2-dibutyl-3,4-dihydro-5-hydroxy-1(2H)-naphthalenone (9.59 g) in dry diethyl ether (100 ml) was added lithium aluminium hydride (1.33 g) slowly at 0° C. under a nitrogen atmosphere. The suspension was stirred for 3 hours at 0° C. and then poured into ice. The mixture was acidified with aqueous 1N hydrochloric acid and the separated oil was extracted with diethyl ether. The extract was washed with brine and aqueous sodium bicarbonate solution. The solvent was dried and concentrated in vacuo. The residue was purified by columnchromatography on silica gel (elution by CH2Cl2 and then 2% CH3OH in CH2Cl2) to yield 2,2-dibutyl-5-hydroxy-1,2,3,4-tetrahydro-1-naphthol (9.05 g) as crystals.

Workup

  1. additionpoured into ice
  2. extractionthe separated oil was extracted with diethyl ether
  3. washThe extract was washed with brine and aqueous sodium bicarbonate solution
  4. customThe solvent was dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by columnchromatography on silica gel (
  7. washelution by CH2Cl2

Sources & evidence

ORD record
ord-db49a2c05d1a4bd9a676576a7b62344e
Source dataset
uspto-grants-1991_09
Patent number
US05045548

Reaction notes

Loading…