Sulfuric Acid → HCID 20129926, compound

HRID 64982Notes

Reaction equation

HRID 64982 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[C:12]([CH:14]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:15]1([OH:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)#[N:13].[OH-].[Na+]>O1CCCC1.O1CCCC1.O>[NH2:13][CH2:12][CH:14]([C:15]1([OH:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 112651811-[Cyano(p-chlorophenyl)methyl]cyclohexanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 20129926HCID 20129926, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium aluminum hydride (3.5 g.) was suspended in ice cold tetrahydrofuran (125 ml.) and concentrated sulphuric acid (2.5 ml.) added cautiously, with stirring. After one hour, 1-[cyano(p-chlorophenyl)methyl]cyclohexanol (15 g., 0.06 mole) was dissolved in tetrahydrofuran (100 ml.) and added rapidly dropwise with vigorous stirring and cooling. After a further two hours, a tetrahydrofuran-water mixture (1:1; 30 ml.) was added followed by 10% sodium hydroxide solution (50 ml.). The tetrahydrofuran was decanted and the residue washed well with diethyl ether and ethylacetate. The combined organic solution was dried over anhydrous potassium carbonate and evaporated to an oil (12 g.)

Workup

  1. additionadded rapidly dropwise
  2. stirringwith vigorous stirring
  3. temperaturecooling
  4. waitAfter a further two hours
  5. customThe tetrahydrofuran was decanted
  6. washthe residue washed well with diethyl ether and ethylacetate
  7. dry with materialThe combined organic solution was dried over anhydrous potassium carbonate
  8. customevaporated to an oil (12 g.)

Sources & evidence

ORD record
ord-b0f6b359f90648dd979fb8d0d6eed2f7
Source dataset
uspto-grants-1986_09
Patent number
US04611078

Reaction notes

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