Water → 2-(5,6,7,8-Tetrahydro-1-naphthoxy)ethanol

HRID 2371639Notes

Reaction equation

HRID 2371639 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][O:14]C2CCCCO2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.O1CCCC1.O.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O>[C:1]1([O:11][CH2:12][CH2:13][OH:14])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2735133Sodium Carbonate MonohydrateHCID 151574992-(5,6,7,8-Tetrahydro-1-naphthoxy)-1-tetrahydropyranyloxyethane

Product 1

HCID 151575002-(5,6,7,8-Tetrahydro-1-naphthoxy)ethanolYield 44.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 700 mg (2.54 mmol) of the title product of Example 58 in a mixture of 9 ml of acetic acid, 3 ml of tetrahydrofuran, and 3 ml of water was stirred at 85°-90° C. After 3.5 hours, 4 drops of concentrated sulfuric acid were added and stirring continued for an additional one-half hour. The mixture was permitted to cool, and 4 g of sodium carbonate monohydrate was added. The resulting mixture was partitioned between diethyl ether and water. The organic layer was washed repeatedly with saturated aqueous sodium bicarbonate, with water, and then with brine. The solution was dried over magnesium sulfate, the drying agent was removed by filtration, and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel, using 15% ethyl acetate/toluene as eluent, gave 216 mg of the title compound.

Workup

  1. stirringstirring
  2. waitcontinued for an additional one-half hour
  3. temperatureto cool
  4. customThe resulting mixture was partitioned between diethyl ether and water
  5. washThe organic layer was washed repeatedly with saturated aqueous sodium bicarbonate, with water
  6. dry with materialThe solution was dried over magnesium sulfate
  7. customthe drying agent was removed by filtration
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1b49498a4a22466c8e11f258d0a9b2a0
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

Loading…