Sulfuric Acid → 63327-36-6

HRID 616415Notes

Reaction equation

HRID 616415 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15]1[O:17][CH2:16]1.S(=O)(=O)(O)O>C1COCC1>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][OH:17])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6354Ethylene OxideHCID 15084142HCID 15084142, compound

Product 1

HCID 412113463327-36-6

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 153 g of ethylbromide in 160 ml of abs. THF, is added a suspension of 36 g of magnesium turning in 330 ml of THF, (to obtain a solution of ethyl magnesium bromide) and the reaction mixture cooled to 0° to 5°. To the reaction mixture is then added, dropwise, a solution of 214 g of p-cyclohexylphenylacetylene in 420 ml of abs. THF, over a period of one hour. The resulting thick suspension is diluted with 200 of abs. THF and then refluxed for 1.5 hours. The reaction mixture is then cooled to 0°, and a solution of 62 g ethylene oxide in 420 ml of abs. THF added thereto, dropwise, over a period of one hour. After addition is completed, the reaction mixture is refluxed for 2.5 hours, then decomposed by adding dilute sulfuric acid (5%), and extracted with ether. The combined ether extracts are washed with water, then brine, and evaporated i.v. to dryness to obtain a residue from which is crystallized 4-(p-cyclohexylphenyl)-3-butyn-1 -ol, m.p. 56° - 59° from pentane.

Workup

  1. temperaturecooled to 0° to 5°
  2. additionTo the reaction mixture is then added
  3. additionThe resulting thick suspension is diluted with 200 of abs
  4. temperatureThe reaction mixture is then cooled to 0°
  5. additionAfter addition
  6. temperaturethe reaction mixture is refluxed for 2.5 hours
  7. extractionextracted with ether
  8. washThe combined ether extracts are washed with water
  9. custombrine, and evaporated i.v
  10. customto dryness to obtain a residue from which
  11. customis crystallized 4-(p-cyclohexylphenyl)-3-butyn-1 -ol, m.p. 56° - 59° from pentane

Sources & evidence

ORD record
ord-051d022dc01b4b0e98b4265ca4a757fd
Source dataset
uspto-grants-1978_02
Patent number
US04073936

Reaction notes

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