Hydrochloric Acid → HCID 20377644, compound

HRID 2052310Notes

Reaction equation

HRID 2052310 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].[CH:10]1[C:23]2[C:22](=[O:24])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:25])[C:14]=2[CH:13]=[CH:12][CH:11]=1.Cl>C1(C)C=CC=CC=1.O1CCCC1>[OH:25][C:15]1([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[C:22](=[O:24])[C:23]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6780AnthraquinoneHCID 78054-BromotolueneHCID 5462224Magnesium

Product 1

HCID 20377644HCID 20377644, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A Grignard solution, consisting of 85.5 g (0.5 mol) of 4-bromotoluene and 11.5 g of magnesium filings, is added dropwise to 104 g (0.5 mol) of anthraquinone in 2,000 ml of absolute toluene and 500 ml of absolute tetrahydrofurane at 80° C. After the dropwise addition has ended, the mixture is subsequently stirred for 6 hours at 80° C. The reaction mixture is then hydrolysed in 2,000 ml of ice water, containing hydrochloric acid. The organic phase is separated off, washed with water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The solid residue is recrystallised from acetonitrile. 32.5 g (21% of theory) of 9,10-dihydro-9-hydroxy-9-(4-methylphenyl)-10-oxoanthracene of melting point 203°-209° C. are obtained.

Workup

  1. additionAfter the dropwise addition
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. distillationby distilling off the solvent in vacuo
  7. customThe solid residue is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-cf99ae7af0254a57a4dfeb0d8b46acd7
Source dataset
uspto-grants-1980_01
Patent number
US04183940

Reaction notes

Loading…