Water → HCID 10398790, compound

HRID 654686Notes

Reaction equation

HRID 654686 reaction equation
O[C:2]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[C:13]([OH:15])=[CH:12][CH:11]=[CH:10]2)([CH3:4])[CH3:3].[OH2:16].N1[CH:22]=[CH:21]C=CC=1>C(O)(=O)C>[C:21]([O:15][C:13]1[C:14]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[C:2]([CH3:4])=[CH2:3])[CH:10]=[CH:11][CH:12]=1)(=[O:16])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 10262250HCID 10262250, compound

Product 1

HCID 10398790HCID 10398790, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

11.3 g of 8-(1-hydroxy-1-methyl-1-ethyl)-1-naphthol was dissolved in 24 ml of pyridine, to which 12 ml of anhydrous acetic acid was added. The solution was raised in temperature to 60° C. and heated for 6 hours under agitation. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resulting organic phase was washed with a 2N hydrochloric acid aqueous solution, water and a saturated saline solution in this order, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 3.6 g of the captioned compound as an oily substance.

Workup

  1. additionwas added
  2. temperatureheated for 6 hours under agitation
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resulting organic phase was washed with a 2N hydrochloric acid aqueous solution, water
  5. dry with materiala saturated saline solution in this order, dried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-10504e77714048f58ef71225b6bcbfc3
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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