Sulfuric Acid → HCID 18007034, compound

HRID 463575Notes

Reaction equation

HRID 463575 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[CH2:22](O)[C:23]#[CH:24].S(=O)(=O)(O)O>O>[CH2:24]([O:12][C:11](=[O:13])[CH2:10][CH2:9][C:8]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:14])[C:23]#[CH:22]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7859Propargyl alcoholHCID 671744,4-Bis(4-hydroxyphenyl)valeric acid

Product 1

HCID 18007034HCID 18007034, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21.2 grams of 4,4-bis(4-hydroxyphenyl)pentanoic acid, 50 ml. of propargyl alcohol and 0.3 ml. of concentrated sulfuric acid was stirred at room temperature for 40 hours. The mixture was then poured into 500 ml. of water, with stirring. The oily layer was allowed to settle and the aqueous layer was removed by decantation. The oily layer was washed with water two additional times. Finally, 500 ml. of water containing 10 grams of sodium bicarbonate was added to the oily layer, the product was extracted from the mixture into ether and chromatographed on a silica column (using 10/90 acetone/toluene, by volume, eluent) to give 96.9 grams (41%) of white solid, m.p. 99.5°-101.0° C.

Workup

  1. additionThe mixture was then poured into 500 ml
  2. customthe aqueous layer was removed by decantation
  3. washThe oily layer was washed with water two additional times
  4. additionof water containing 10 grams of sodium bicarbonate was added to the oily layer
  5. extractionthe product was extracted from the mixture into ether
  6. customchromatographed on a silica column (using 10/90 acetone/toluene, by volume, eluent)

Sources & evidence

ORD record
ord-812c92f3a2ef4d5c85a4958132181add
Source dataset
uspto-grants-1985_05
Patent number
US04520379

Reaction notes

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