Sulfuric Acid → (4-Phenylcyclohexyl)methanol

HRID 1248095

Reaction equation

HRID 1248095 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O.C(OCC)(=O)C.S(=O)(=O)(O)O>O1CCCC1.O>[C:17]1([CH:14]2[CH2:15][CH2:16][CH:11]([CH2:9][OH:8])[CH2:12][CH2:13]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 178501033HCID 178501033, compound

Product 1

HCID 3100608(4-Phenylcyclohexyl)methanolYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

Dry tetrahydrofuran (THF)(420 ml) was added to lithium aluminum hydride (11.1 g, 0.293 mol), and while the mixture was vigorously agitated, there was dropwise added a soltuion obtained by dissolving trans-4-phenylcyclohexanecarboxylic acid methyl ester (II) (64.0 g, 0.293 mol) in THF (70 ml), at a reaction temperature kept at 20° C. or lower. After completion of the addition, the reaction mixture was warmed up to 55° C., followed by reacting it for 2 hours and cooling. Ethyl acetate (12 ml) and water (100 ml) were then added, followed by adding a 1N aqueous solution of sulfuric acid (350 ml) to dissolve inorganic matter, separating the resulting organic layer and aqueous layer from one another, adding n-heptane (200 ml) to extract the organic layer, washing the extract solution with water 500 ml), then washing with a 2% aqueous solution of Na2CO3, further washing with water until the aqueous layer became neutral, distilling off n-heptane and THF, recrystallizing the resulting solid as residue from n-heptane (20 ml), filtering off crystals and drying to obtain 4-phenylcyclohexylmethanol (III) (51.4 g). M.P. 47.3°~48.5° C.

Workup

  1. additionthere was dropwise added a soltuion
  2. customobtained
  3. customkept at 20° C.
  4. additionAfter completion of the addition
  5. customfor 2 hours
  6. temperaturecooling
  7. dissolutionto dissolve inorganic matter
  8. customseparating the resulting organic layer and aqueous layer from one another,
  9. additionadding n-heptane (200 ml)
  10. extractionto extract the organic layer
  11. washwashing the extract solution with water 500 ml),
  12. washthen washing with a 2% aqueous solution of Na2CO3
  13. washfurther washing with water until the aqueous layer
  14. distillationdistilling off n-heptane and THF
  15. customrecrystallizing the resulting solid as residue from n-heptane (20 ml)
  16. filtrationfiltering off crystals
  17. customdrying

Sources & evidence

ORD record
ord-4c92742c633b4b8cbb9918259bce6434
Source dataset
uspto-grants-1985_06
Patent number
US04522741

Linked notes

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