Sulfuric Acid → 1-[(2,2,6-Trimethylcyclohexyl)oxy]pentan-2-OL

HRID 365172

Reaction equation

HRID 365172 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[OH:10].[H-].[Na+].[O:13]1[CH:15]([CH2:16][CH2:17][CH3:18])[CH2:14]1.OS(O)(=O)=O>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[O:10][CH2:14][CH:15]([OH:13])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 13853Oxirane, 2-propyl-HCID 24758Sodium hydrideHCID 125371292,2,6-Trimethylcyclohexan-1-ol

Product 1

HCID 30211651-[(2,2,6-Trimethylcyclohexyl)oxy]pentan-2-OLYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.0 g of 2,6,6-trimethyl-cyclohexanol and 0.354 g of sodium hydride was heated for 24 hours at 80° in 10 ml of anhydrous toluene. 1.2 G of 1,2-epoxy-pentane were then added to the thus obtained solution and heating at 80° was maintained for 24 additional hours. After cooling, the reaction mixture was poured onto crushed iced, acidified with diluted H2SO4, whereupon the organic phase was washed with brine until neutrality. After evaporation of the volatile parts and distillation of the residue in a a bulb apparatus (bath temperature: 140°/7 Pa), the desired product was obtained in yield of about 75%. An analytical sample was purified by preparative gas chromatography.

Workup

  1. temperatureheating at 80°
  2. temperaturewas maintained for 24 additional hours
  3. temperatureAfter cooling
  4. additionthe reaction mixture was poured
  5. customonto crushed iced
  6. washwas washed with brine until neutrality
  7. customAfter evaporation of the volatile parts and distillation of the residue in a a bulb apparatus (bath temperature: 140°/7 Pa)

Sources & evidence

ORD record
ord-f4e9b88607ef45dab5742f8501ec720f
Source dataset
uspto-grants-1986_08
Patent number
US04608445

Linked notes

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