Sulfuric Acid → HCID 22251262, compound

HRID 463574Notes

Reaction equation

HRID 463574 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)[CH:23]=[CH2:24].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])[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 671744,4-Bis(4-hydroxyphenyl)valeric acid

Product 1

HCID 22251262HCID 22251262, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 85.8 grams of 4,4-bis-(4-hydroxyphenyl)pentanoic acid, 200 ml. of allyl alcohol and 2 ml. of concentrated sulfuric acid was heated to 50° C. and maintained at the temperature, with stirring, for 20 hours. The mixture was then poured into 1500 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, a 1500 ml. portion of water was added to the oil and the mixture was stirred until the viscous oil solidified. The solid was separated from the water, pulverized and stirred one hour with 1000 ml. of water containing 16.8 grams of sodium bicarbonate. The product was filtered and washed with water until the filtrate was neutral. Yield: 86.6 grams (88.5%) of off white solid, m.p. 83°-85° C.

Workup

  1. temperaturemaintained at the temperature
  2. additionThe mixture was then poured into 1500 ml
  3. customthe aqueous layer was removed by decantation
  4. washThe oily layer was washed with water two additional times
  5. additionportion of water was added to the oil
  6. stirringthe mixture was stirred until the viscous oil
  7. customThe solid was separated from the water
  8. stirringstirred one hour with 1000 ml
  9. filtrationThe product was filtered
  10. washwashed with water until the filtrate

Sources & evidence

ORD record
ord-45273e9eb89440b8a1fdb7598ab291c2
Source dataset
uspto-grants-1985_05
Patent number
US04520379

Reaction notes

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