Sulfuric Acid → (3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-ol

HRID 2352478Notes

Reaction equation

HRID 2352478 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12]([CH3:14])=[O:13].[OH-].[Na+].S(=O)(=O)(O)O>>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[CH:12]([OH:13])[CH3:14]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 638014I2-Ionone

Product 1

HCID 5373729(3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-ol

Procedure

β-Ionol was synthesized from β-ionone as described above for synthesis for aα-ionol with the following modification: 20% sodium hydroxide solution was used to hydrolyze the reaction complex in place of the sulfuric acid solution and the separated organic layer was neutralized by washing with water. α-Ionol thus prepared had the following constants: boiling point, 78° C./0.2 mm; nD25 1.4975; yield 5.9 g. Infrared spectrum and GC retention time was identical to that of a commercially available sample.

Workup

  1. washby washing with water
  2. customα-Ionol thus prepared
  3. custompoint, 78° C./0.2 mm

Sources & evidence

ORD record
ord-f06844a67396475bbaee383b72ced181
Source dataset
uspto-grants-1989_10
Patent number
US04877607

Reaction notes

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