Hydroquinone → HCID 67630716, compound

HRID 1720946Notes

Reaction equation

HRID 1720946 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([C:7](C=CC(O)=O)=[O:8])=[CH:3][CH:2]=1.C=CC=C.C1(C=CC(O)=CC=1)[OH:20].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[C:27]1([CH3:33])[CH:32]=[CH:31][C:30]([C@H:5]2[C@H:4]([C:7]([OH:8])=[O:20])[CH2:3][CH:2]=[CH:1][CH2:6]2)=[CH:29][CH:28]=1

Participants

5

Reactant 4

HCID 785HydroquinoneHCID 1140Toluene2×HCID 78451,3-ButadieneHCID 69110524849-45-4

Product 1

HCID 67630716HCID 67630716, compound

Procedure

275 g (1.695 mol) of 3-(4-toluoyl)acrylic acid (commercially available from Aldrich) is reacted according to a known process [cf.: Eur. J. Med. Chem. 11, 493 (1976)]at about 200° C. and about 20 bar for 22 h with 580 ml of 1,3-butadiene (measured in condensed form) in 480 ml of toluene with the addition of 3 g of hydroquinone. The crude mixture is diluted with toluene and extracted with 0.5M aqueous sodium hydroxide solution. The aqueous phases are then acidified with 1M hydrochloric acid and extracted with ether. The ethereal solutions are dried with sodium sulphate, evaporated and redissolved in toluene. After boiling with 5 g of active carbon for 15 minutes, the mixture is filtered off hot with suction and the solvent is evaporated down to about 120-160 ml; at 0°-4° C. 124 g (573 mmol) of product crystallise out. The filtrate is concentrated somewhat further and cooled again for recrystallisation. On repeating this process altogether a further 42 g (194 mmol) of product are obtained.

Workup

  1. extractionextracted with 0.5M aqueous sodium hydroxide solution
  2. extractionextracted with ether
  3. dry with materialThe ethereal solutions are dried with sodium sulphate
  4. customevaporated
  5. dissolutionredissolved in toluene
  6. filtrationthe mixture is filtered off hot with suction
  7. customthe solvent is evaporated down to about 120-160 ml
  8. customat 0°-4° C
  9. concentrationThe filtrate is concentrated somewhat further
  10. temperaturecooled again for recrystallisation
  11. customare obtained

Sources & evidence

ORD record
ord-ba9633cf48bb4125be29cbeac988c371
Source dataset
uspto-grants-1996_04
Patent number
US05508299

Reaction notes

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