Tetrahydrofuran → HCID 19094984, compound

HRID 2254957Notes

Reaction equation

HRID 2254957 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7](/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5]1.O1CCCC1>O>[CH:10](/[CH:7]1[CH2:6][CH2:5][CH:4]([CH:3]=[O:2])[CH2:9][CH2:8]1)=[CH:11]\[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 19739325HCID 19739325, compound

Product 1

HCID 19094984HCID 19094984, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.75 g of 1-(methoxymethylene)-4-(1E-pentenyl)cyclohexane (crude product from paragraph a) were heated to boiling for 30 minutes with 100 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) and then stirred overnight at room temperature. The mixture was subsequently treated with 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The extracts were washed with dilute sodium hydrogen carbonate solution and water and the aqueous phases were back-extracted with diethyl ether. The organic phases were dried over magnesium sulphate and evaporated. Low-pressure chromatography of the residual yellowish liquid (2.5 g) on silica gel with petroleum ether and ethyl acetate/petroleum ether (vol. 3:97) gave 1.65 g (76%) of 4-(1E-pentenyl)cyclohexanecarboxaldehyde.

Workup

  1. extractionextracted three times with 100 ml of diethyl ether each time
  2. washThe extracts were washed with dilute sodium hydrogen carbonate solution and water
  3. extractionthe aqueous phases were back-extracted with diethyl ether
  4. dry with materialThe organic phases were dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-df9f1c37b85347039bcde1b8613e9b96
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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