Ethylene Glycol → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-3-cyclohexenone ethylene ketal

HRID 1660056Notes

Reaction equation

HRID 1660056 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:24](O)[CH2:25][OH:26].C1(C=CC(O)=CC=1)O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:25]1[O:26][C:18]2([CH2:19][CH2:20][CH:21]=[C:16]([C:13]3[CH:14]=[CH:15][C:10]([C:2]([CH3:1])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][C:12]=3[OH:23])[CH2:17]2)[O:22][CH2:24]1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 785HydroquinoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 127882083-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenone

Product 1

HCID 127883053-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-3-cyclohexenone ethylene ketal

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 500 mg. (1.59 mmole) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenone, 7.8 g. (127 mmole) of ethylene glycol, 375 mg. (3.18 mmole) of hydroquinone and 50 mg. (0.263 mmole) of p-toluenesulfonic acid monohydrate in 50 ml of benzene was heated at reflux for 12 hours using a Dean-Stark condensor filled with 3 A molecular sieves. The reaction was cooled and added to 500 ml. saturated sodium bicarbonate. The quenched mixture was extracted with three 150 ml. portions of ether, dried over magnesium sulfate and evaporated to a solid. This solid was purified via column chromatography on 50 g. of silica gel eluted with 50% etherpetroleum ether to yield (after crystallization from pentane) 393 mg. (69%) of the title product.

Workup

  1. temperatureat reflux for 12 hours
  2. additionfilled with 3 A molecular sieves
  3. temperatureThe reaction was cooled
  4. additionadded to 500 ml
  5. extractionThe quenched mixture was extracted with three 150 ml
  6. dry with materialportions of ether, dried over magnesium sulfate
  7. customevaporated to a solid
  8. customThis solid was purified via column chromatography on 50 g
  9. washof silica gel eluted with 50% etherpetroleum ether
  10. customto yield
  11. custom(after crystallization from pentane) 393 mg

Sources & evidence

ORD record
ord-2019c3f74bdc4b95a570c24a15d11b92
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

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