Sodium hydride → HCID 68058524, compound

HRID 1035688Notes

Reaction equation

HRID 1035688 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].C([C:19](CC)(P(=O)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>O1CCCC1>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([CH:5]2[CH2:6][CH2:7][C:2](=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:3][CH2:4]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 45989164-(4'-Hydroxyphenyl)cyclohexanoneHCID 19386061HCID 19386061, compound

Product 1

HCID 68058524HCID 68058524, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

10 g of 4-(4-hydroxyphenyl)cyclohexanone (52.56 mmol, 1 eq.) are placed in 150 mL of tetrahydrofuran in a 250 mL round-bottomed flask under nitrogen. The solution is cooled to 4° C. on an ice bath and 2.523 g of 60% sodium hydride (63.08 mmol, 1.2 eq.) are added portionwise. 14.141 g of ethyl diethylphosphoacetate (63.08 mmol, 1.2 eq.) are placed in 150 mL of tetrahydrofuran in another 250 mL round-bottomed flask under nitrogen. This second solution is cooled on an ice bath and 2.523 g of 60% sodium hydride (63.08 mmol, 1.2 eq.) are added portionwise. The ice baths are removed and the media are stirred at room temperature for 30 minutes. The 4-(4-hydroxyphenyl)-cyclohexanone solution is added to the ethyl diethylphosphoacetate solution. The reaction medium is stirred for 1 hour 30 minutes. Saturated aqueous ammonium chloride solution is added and the reaction medium is extracted three times with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated to give 13.5 g of ethyl [4-(4-hydroxyphenyl)cyclohexylidene]acetate. M+H+=261.

Workup

  1. temperatureThis second solution is cooled on an ice bath
  2. customThe ice baths are removed
  3. additionThe 4-(4-hydroxyphenyl)-cyclohexanone solution is added to the ethyl diethylphosphoacetate solution
  4. stirringThe reaction medium is stirred for 1 hour 30 minutes
  5. additionSaturated aqueous ammonium chloride solution is added
  6. extractionthe reaction medium is extracted three times with ethyl acetate
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a8f640013464452e8591c77ce0e54a19
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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