Hydrochloric Acid → 4,4,6-Trimethylbicyclo[4.2.0]octan-2-ol

HRID 442068Notes

Reaction equation

HRID 442068 reaction equation
[BH4-].[Na+].CC(O)C.[CH3:7][C:8]1([CH3:18])[CH2:15][C:14]2([CH3:16])[CH:11]([CH2:12][CH2:13]2)[C:10](=[O:17])[CH2:9]1.Cl>O.C1(C)C=CC=CC=1>[CH3:7][C:8]1([CH3:18])[CH2:15][C:14]2([CH3:16])[CH:11]([CH2:12][CH2:13]2)[CH:10]([OH:17])[CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776Isopropanol2×HCID 4311764Sodium borohydrideHCID 227655154,4,6-Trimethylbicyclo[4.2.0]octan-2-one

Product 1

HCID 64548754,4,6-Trimethylbicyclo[4.2.0]octan-2-olYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

To a 2-liter 3-necked flask fitted with a mechanical stirrer, additional funnel, reflux condenser and drying tube was added 15 g. (0.39 mole) of sodium borohydride and 500 ml. 2-propanol. To this solution was slowly added 218.6 g. (1.317 moles) of 4,4,6-trimethylbicyclo[4.2.0]octane-2-one in 50 ml. of 2-propanol. After 2 hours, about 200 ml. of water was added. The mixture was stirred an additional 1 hour, then about 35 ml. concentrated hydrochloric acid was added. After another 1 hour of stirring, 400 ml. of toluene and 500 ml. of water were added. The layers were separated and the organic layer was washed three times with 100 ml. of water. The combined water layers were extracted with toluene. The toluene layers were combined and dried over potassium carbonate. The solution was concentrated in vacuo and the residue distilled through a 25 cm. Vigreux--column to yield 215.8 g. (1.284 moles, 97.5 % yield) of 4,4,6-trimethylbicyclo [4.2.0]octane-2-ol. IR: 3360 cm-1.

Workup

  1. customTo a 2-liter 3-necked flask fitted with a mechanical stirrer, additional funnel
  2. temperaturereflux condenser
  3. customdrying tube
  4. additionwas added 15 g
  5. stirringAfter another 1 hour of stirring
  6. customThe layers were separated
  7. washthe organic layer was washed three times with 100 ml
  8. extractionThe combined water layers were extracted with toluene
  9. dry with materialdried over potassium carbonate
  10. concentrationThe solution was concentrated in vacuo
  11. distillationthe residue distilled through a 25 cm
  12. customVigreux--column to yield 215.8 g

Sources & evidence

ORD record
ord-84cbe9df9c6f45aa82fa1b205f8e8cd5
Source dataset
uspto-grants-1977_08
Patent number
US04044057

Reaction notes

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