HCID 178440758, compound → HCID 178445603, compound

HRID 1980110Notes

Reaction equation

HRID 1980110 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:12](=[O:23])[C:13]3[C:18]([C:19](=[O:22])[C:20]=2[OH:21])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>S(=O)(=O)(O)O>[C:1]([C@@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[C:12](=[O:23])[C:13]3[C:18]([C:19](=[O:22])[C:20]=2[OH:21])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 178440758HCID 178440758, compound

Product 1

HCID 178445603HCID 178445603, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

An approximately 1:1 cis/trans mixture of 2-(4'-t-butylcyclohexyl)-3-hydroxy-1,4-naphthoquine (see Example 1) (10 g) was dissolved in concentrated sulphuric acid (100 ml) and the solution maintained at various temperatures for various periods of times as shown below. At the end of the reaction the reaction mixture was cooled and poured dropwise into ice/water to provide crude product which was purified by recrystallisation as previously described and/or column chromatography. The isomers ratios of the product were determined by NMR, GLC.; the results shown below.

Workup

  1. temperaturethe solution maintained at various temperatures for various periods of times
  2. customAt the end of the reaction the reaction mixture
  3. temperaturewas cooled
  4. customto provide crude product which
  5. customwas purified by recrystallisation

Sources & evidence

ORD record
ord-763b2562dd8e4035bd19e0d3195c1ed1
Source dataset
uspto-grants-1984_11
Patent number
US04485117

Reaction notes

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