Hydrochloric Acid → HCID 19967162, compound

HRID 976344Notes

Reaction equation

HRID 976344 reaction equation
Cl.[CH:2]([C:4]1[C:5]([O:18]COC)=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)=[O:3].O>O1CCCC1>[CH:2]([C:4]1[C:5]([OH:18])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:14])([CH3:15])[C:12]=2[CH:13]=1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19967148HCID 19967148, compound

Product 1

HCID 19967162HCID 19967162, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A 10% aqueous solution of hydrochloric acid was added to 30 ml of a solution of 2.4 g of 3-formyl-5,6,7,8-tetrahydro-2-methoxymethoxy-5,5,8,8-tetramethylnaphthalene in tetrahydrofuran at room temperature. The obtained mixture was stirred at 50° C. for 4 hours, followed by the addition thereto of 30 ml of water. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to removd the solvent. The residue was purified by silica gel chromatography (developer: 10% diethyl ether/n-hexane) to give 1.8 g of the title compound as a colorless oil.

Workup

  1. additionfollowed by the addition
  2. extractionThe obtained mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with a saturated aqueous solution of common salt
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customThe residue was purified by silica gel chromatography (developer: 10% diethyl ether/n-hexane)

Sources & evidence

ORD record
ord-46f264bacb524b0784b5142c5f63e913
Source dataset
uspto-grants-1997_03
Patent number
US05612356

Reaction notes

Loading…