Isopropanol → HCID 19380505, compound

HRID 653369Notes

Reaction equation

HRID 653369 reaction equation
[CH:1](/[CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]=[O:13])[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].[Cr](O)(O)(=O)=[O:15].C(O)(C)C>CC(C)=O>[CH:1](/[CH:6]1[CH2:7][CH2:8][CH:9]([C:12]([OH:15])=[O:13])[CH2:10][CH2:11]1)=[CH:2]\[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24425Chromic Acid2×HCID 19094984HCID 19094984, compound

Product 1

HCID 19380505HCID 19380505, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.6 g of 4-(trans-1-pentenyl)cyclohexanecarboxaldehyde in 120 ml of acetone was cooled to -10° C., treated dropwise with 8N chromic acid (about 10 ml) until the colour of the mixture remained brown-orange and stirred for 1 hour. Excess chromic acid was reduced by the addition of isopropanol. The green solution was subsequently partitioned three times in water/methylene chloride. The organic extracts were washed twice with water and the wash-water was back-extracted with methylene chloride. The organic phases were dried over magnesium sulphate and evaporated. The pale brown crystalline residue (2.01 g) was dissolved partially in 20 ml of petroleum ether. Undissolved residue was filtered off and the filtrate was evaporated. Recrystallization of the resulting residue from 60 ml of petroleum ether at -78° C. gave 866 mg (49.5%) of 4-(trans-1-pentenyl)cyclohexanecarboxylic acid as white crystals.

Workup

  1. customThe green solution was subsequently partitioned three times in water/methylene chloride
  2. washThe organic extracts were washed twice with water
  3. washthe wash-water
  4. extractionwas back-extracted with methylene chloride
  5. dry with materialThe organic phases were dried over magnesium sulphate
  6. customevaporated
  7. dissolutionThe pale brown crystalline residue (2.01 g) was dissolved partially in 20 ml of petroleum ether
  8. filtrationwas filtered off
  9. customthe filtrate was evaporated
  10. customRecrystallization of the resulting residue from 60 ml of petroleum ether at -78° C.

Sources & evidence

ORD record
ord-4ae3c2ee0f914f1c947e4226178e2472
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Reaction notes

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