Acetic Acid → 147331-60-0

HRID 437042Notes

Reaction equation

HRID 437042 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[CH2:5]1[C:14]2[C:9](=CC=CC=2)[CH:8]=[CH:7][CH2:6]1.[OH2:15].II.[C:18]([OH:21])(=O)[CH3:19]>C([O-])(=O)C.[Ag+]>[C:1]1([OH:4])[C:2]2[CH2:19][C@H:18]([OH:21])[C@H:5]([OH:15])[CH2:6][C:7]=2[CH:8]=[CH:9][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic Acid3×HCID 807IodineHCID 962WaterHCID 70602138HCID 70602138, compound

Product 1

HCID 51656356147331-60-0

Reagents, catalysts & solvents 1

HCID 11246Silver acetateCatalyst

Procedure

The corresponding cis isomer of formula II can be prepared by dissolving a dihydronaphthalene acetate of formula X in acetic acid and water (from 92 to 98% acetic acid, preferably 96% acetic acid), and then treating the solution with silver acetate and iodine and heating under nitrogen (as described for the preparation of the trans-isomer) to form the cis-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol having the formula ##STR16## after basic hydrolysis. A compound of formula XV can be converted to the 2,3-cis-1,2,3,4-tetrahydro-5-[2,3-(epoxy)propoxy]-2,3-naphthalenediol, which in turn can be converted to the 2,3-cis-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(alkylamino)-propoxy]-2,3-naphthalenediol in a manner similar to that described with respect to the preparation of the corresponding trans isomer.

Workup

  1. temperatureheating under nitrogen (
  2. customas described for the preparation of the trans-isomer)

Sources & evidence

ORD record
ord-2d905cdce4cc4e56bb9f4e2c1134605d
Source dataset
uspto-grants-1977_06
Patent number
US04029676

Reaction notes

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