Benzene → [1,1′-Biphenyl]-3,5-diol

HRID 329224Notes

Reaction equation

HRID 329224 reaction equation
COC(=O)[C:4]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([OH:20])=[C:6](C(OC)=O)[C:5]=1[OH:21].Cl.C1C=CC=CC=1>O.[OH-].[Na+].CCOCC>[C:14]1([C:13]2[CH:12]=[C:11]([OH:20])[CH:6]=[C:5]([CH:4]=2)[OH:21])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 11023038HCID 11023038, compound

Product 1

HCID 604248[1,1′-Biphenyl]-3,5-diolYield 54.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

6.00 g (0.0199 mole) of 2,4-dihydroxy-6-phenyl-isophthalic acid dimethyl ester is dissolved under nitrogen in 40 ml of water and 40 ml of 2N sodium hydroxide solution. The light-red solution is refluxed for one hour; it is then cooled with an ice bath and carefully acidified with 8.0 ml of concentrated hydrochloric acid (carbon dioxide evolution). The mixture is then refluxed and boiled for 14 hours in a nitrogen atmosphere. The emulsion obtained after cooling is extracted twice with 100 ml of ether each time. The combined ether layers are dried with magnesium sulphate and concentrated in vacuo to obtain 3.98 g of crude product in the form of yellow crystals. This crude product is dissolved in 20 ml of ether; 50 ml of benzene is added and the ether then distilled off. 5-Phenylresorcinol crystallises out on standing. After cooling, there is added 50 ml of hexane, and the crystals are filtered off under suction; this yields 2.44 g of cream-coloured crystals, M.P. 154°-158°. Repeated crystallisation from 40 ml of benzene with the addition of 40 ml of hexane yields 2.03 g of 5-phenylresorcinol as colourless crystals, M.P. 157° - 158°.

Workup

  1. temperatureThe light-red solution is refluxed for one hour
  2. temperatureit is then cooled with an ice bath
  3. temperatureThe mixture is then refluxed
  4. customThe emulsion obtained
  5. temperatureafter cooling
  6. extractionis extracted twice with 100 ml of ether each time
  7. dry with materialThe combined ether layers are dried with magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customto obtain 3.98 g of crude product in the form of yellow crystals
  10. distillationthe ether then distilled off
  11. custom5-Phenylresorcinol crystallises out
  12. temperatureAfter cooling
  13. additionthere is added 50 ml of hexane
  14. filtrationthe crystals are filtered off under suction
  15. customcrystallisation from 40 ml of benzene
  16. additionwith the addition of 40 ml of hexane

Sources & evidence

ORD record
ord-80d9218f69944306b836dc756a4bacc7
Source dataset
uspto-grants-1977_04
Patent number
US04020098

Reaction notes

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