Hydrochloric Acid → 2,3-Dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butan-1-ol

HRID 1979110Notes

Reaction equation

HRID 1979110 reaction equation
[CH3:1][CH:2]([CH:5]([CH3:15])[CH2:6][CH:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:14])[CH3:13])[CH:3]=[O:4].[BH4-].[Na+].Cl>C(O)C>[CH3:1][CH:2]([CH:5]([CH3:15])[CH2:6][CH:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:13])[CH3:14])[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 154310452,3-Dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butanal

Product 1

HCID 154310462,3-Dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butan-1-olYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 18.0 g (86 mmol) of 2,3-dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butanal in 50 ml of ethanol was added dropwise at 0° C. to 45.0 g (0.11 mol) of sodium borohydride suspended in 200 ml of the same solvent. After 18 hours of stirring at room temperature 100 ml of 1.0 N aqueous hydrochloric acid was added dropwise at 0° C. The reaction mixture was extracted with 200 ml of MTBE, the extract washed with with 3×100 ml of brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled at 82-86° C./0.1 Torr to give 14.1 g (78% yield) of 2,3-dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butan-1-ol.

Workup

  1. additionwas added dropwise at 0° C
  2. extractionThe reaction mixture was extracted with 200 ml of MTBE
  3. washthe extract washed with with 3×100 ml of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was distilled at 82-86° C./0.1 Torr

Sources & evidence

ORD record
ord-d76cacae79d74640957781c6d77ddbcd
Source dataset
uspto-grants-2001_05
Patent number
US06239314B1

Reaction notes

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