Sulfuric Acid → HCID 14511979, compound

HRID 346294Notes

Reaction equation

HRID 346294 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14](O)[CH:15]=[CH2:16].[C:18]1(C)[CH:23]=CC=C[CH:19]=1.S(=O)(=O)(O)O>COC1C=CC(O)=CC=1.O>[OH:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:23][CH:18]=[CH2:19])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH2:14][CH:15]=[CH2:16])=[O:8]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 7858Allyl AlcoholHCID 692575-Hydroxyisophthalic acid

Product 1

HCID 14511979HCID 14511979, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 962WaterSolvent

Procedure

Into a reaction vessel equipped with a stirrer, condenser and thermometer was placed 0.2 mole of 5-hydroxyisophthalic acid. Thereto were added 0.6 mole of allyl alcohol, 300 ml of toluene, 1.3 g of sulfuric acid and 0.2 g of p-methoxyphenol and the mixture was refluxed with heating. A mixture of toluene and water was distilled off and cooled with a condenser, and toluene was separated from water and returned contineously to the reaction vessel. The mixture was heated for 8 hours and then allowed to cool. At this point, total of distilled water was 7 ml. After the reaction mixture was washed with a saturated aqueous solution of sodium chloride until the aqueous layer did not indicate acidic, toluene was distilled at a reduced pressure. The resulting concentrate was distilled at a reduced pressure to obtain 27 g (yield 52%) of diallyl 5-hydroxyisophthalate. b.p. 202°~205° C./5 mm Hg.

Workup

  1. customInto a reaction vessel equipped with a stirrer, condenser
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating
  4. distillationwas distilled off
  5. temperaturecooled with a condenser
  6. customtoluene was separated from water
  7. temperatureThe mixture was heated for 8 hours
  8. temperatureto cool
  9. washAfter the reaction mixture was washed with a saturated aqueous solution of sodium chloride until the aqueous layer
  10. distillationtoluene was distilled at a reduced pressure
  11. concentrationThe resulting concentrate
  12. distillationwas distilled at a reduced pressure

Sources & evidence

ORD record
ord-d548b70d6c284399bab3ad8dc6db85f7
Source dataset
uspto-grants-1991_10
Patent number
US05061770

Reaction notes

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