Water → HCID 14986463, compound

HRID 654695Notes

Reaction equation

HRID 654695 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH3:19])[CH:12]=[CH:11][C:10]=1[C:20]([CH3:23])(O)[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>O1CCCC1.Cl>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH3:19])[CH:12]=[CH:11][C:10]=1[C:20]([CH3:23])=[CH2:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 14986462HCID 14986462, compound

Product 1

HCID 14986463HCID 14986463, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.8 g of 1-(1-benzyloxy-8-methyl-2-naphthyl)-1-methyl-1-ethanol was dissolved in 20 ml of tetrahydrofuran, to which 30 ml of 3N hydrochloric acid was added, followed by refluxing for 2 hours. The reaction solution was returned to room temperature, to which water was added, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (4% ethyl acetate/hexane) to obtain 1.0 g of the captioned compound as a yellowish green oily substance.

Workup

  1. additionwas added
  2. temperatureby refluxing for 2 hours
  3. additionwas added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resultant organic phase was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (4% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-370fa229d3d94e3fa9d875a50015d6dd
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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