Catechol → HCID 20037275, compound

HRID 1904550Notes

Reaction equation

HRID 1904550 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][C:10]1[CH:11]=CC(C)=[CH:14][CH:15]=1.P(=O)(O)(O)O.C=CC(=C)C>O.CCCCCC>[CH3:9][C:10]1([CH3:11])[CH2:15][CH2:14][C:8]2[CH:7]=[CH:6][CH:5]=[C:3]([OH:4])[C:1]=2[O:2]1

Participants

7

Reactant 4

HCID 289CatecholHCID 1004Phosphoric AcidHCID 6557IsopreneHCID 7809P-Xylene

Product 1

HCID 20037275HCID 20037275, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

While a mixture of 10 g of catechol, 50 ml of p-xylene, 25 ml of hexane, 1 ml of phosphoric acid and 0.3 ml of water was heated at 100° C., 7.3 g of isoprene was added dropwise over 10 minutes, and the reaction was further carried out for 7 hours. After cooling, the resulting precipitate was separated by filtration. The filtrate was concentrated, and purified by column chromatography to give 1.7 g (yield 11%) of the product as a pale pink liquid.

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitate was separated by filtration
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-48000f66db4c4ffa9119200210d3b5ec
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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