Sulfuric Acid → (4-Phenylcyclohexyl)methanol

HRID 1262480

Reaction equation

HRID 1262480 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.CCCCCCC.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

8

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 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8900HeptaneSolvent

Conditions

Temperature
55 °C

Procedure

Dry tetrahydrofuran (THF) (420 ml) was added to lithiumaluminum hydride (11.1 g, 0.293 mol) and the mixture was vigorously agitated, followed by dropwise adding to the mixture, a solution obtained by dissolving trans-4-phenylcyclohexanecarboxylic acid methyl ester (II) (64.0 g, 0.293 mol) in THF (70 ml), while keeping the reaction temperature at 20° C. or lower. After completion of the dropwise addition, the reaction mixture was warmed up to 55° C., reacted for 2 hours and cooled, followed by adding ethyl acetate (12 ml) and water (100 ml), and then adding 18% sulfuric acid (350 ml) to form two separated layers of a tetrahydrofuran layer and an aqueous layer. n-Heptane (200 ml) was added to the former layer and the mixture was transferred into a separating funnel, followed by washing with water (500 ml), washing with 2% aqueous solution of sodium carbonate (500 ml), further washing with water till the aqueous layer became neutral, distilling off n-heptane and THF, recrystallizing solid as still residue from n-heptane (20 ml), filtering off the resulting crystals and drying to obtain 4-phenylcyclohexylmethanol (III) (51.4 g). M.P. 47.3°~48.5° C.

Workup

  1. additionby dropwise adding to the mixture
  2. customa solution obtained
  3. customat 20° C.
  4. additionAfter completion of the dropwise addition
  5. customreacted for 2 hours
  6. temperaturecooled
  7. customthe mixture was transferred into a separating funnel
  8. washby washing with water (500 ml)
  9. washwashing with 2% aqueous solution of sodium carbonate (500 ml)
  10. washfurther washing with water till the aqueous layer
  11. distillationdistilling off n-heptane and THF
  12. customrecrystallizing solid as still residue from n-heptane (20 ml)
  13. filtrationfiltering off the resulting crystals
  14. customdrying

Sources & evidence

ORD record
ord-cb836e5c00974092aa8e3dce0898ba1d
Source dataset
uspto-grants-1984_06
Patent number
US04452719

Linked notes

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