1-Methoxy-4-(4-hydroxybutyl)cyclohexa-1,4-diene → 4-(4-Hydroxybutyl)cyclohex-3-ene-1-one

HRID 465551Notes

Reaction equation

HRID 465551 reaction equation
C[O:2][C:3]1[CH2:8][CH:7]=[C:6]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH2:5][CH:4]=1>S(=O)(=O)(O)O>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH:5]=1

Participants

3

Reactant 1

HCID 103523271-Methoxy-4-(4-hydroxybutyl)cyclohexa-1,4-diene

Product 1

HCID 102411954-(4-Hydroxybutyl)cyclohex-3-ene-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A suspension of 4.76 g of 1-methoxy-4-(4-hydroxybutyl)-cyclohexa-1,4-diene in 75 ml 1N sulfuric acid is stirred at room temperature for 1.5 h and extracted with methylene chloride (2×40 ml). The combined organic extracts are washed with saturated sodium bicarbonate, dried (MgSO4), filtered and subjected to evaporation to obtain 4-(4-hydroxybutyl)-cyclohex-3-ene-1-one as an oil.

Workup

  1. extractionextracted with methylene chloride (2×40 ml)
  2. washThe combined organic extracts are washed with saturated sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customsubjected to evaporation

Sources & evidence

ORD record
ord-0b2739bfec4247b3a76dd5c2e720b8f1
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

Loading…