Hydrochloric Acid → (+/-)-9,9'-spirobixanthene-1,1'-diol

HRID 2236130Notes

Reaction equation

HRID 2236130 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5](OC2C=CC=CC=2)[C:4]=1[C:16]([C:18]1[C:23]([O:24]C2C=CC=CC=2)=[CH:22][CH:21]=[CH:20][C:19]=1[O:31]C)=O.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[C:19]1([OH:31])[C:18]2[C:16]3([C:4]4[C:3]([OH:2])=[CH:8][CH:7]=[CH:6][C:5]=4[O:2][C:3]4[C:4]3=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:18]=3)[O:24][C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 57841213Bis(2-methoxy-6-phenoxyphenyl)methanone

Product 1

HCID 12127926(+/-)-9,9'-spirobixanthene-1,1'-diolYield 146.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2 (1.0 g, 2.3 mmol) in dry toluene (20 mL) was added AlCl3 (1.9 g, 14.3 mmol). The solution was warmed slowly and refluxed for 30 minutes. Then it was cooled to 0° C. and concentrated aqueous HCl (20 mL) was introduced with vigorous stirring. After refluxing for 1 hour, the reaction mixture was extracted with EtOAc, washed with concentrated HCl, water, aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated. Flash chromatography (eluting with CH2Cl2) gave 3 as light-yellow powder (0.64 g, yield 72%).

Workup

  1. temperatureThe solution was warmed slowly
  2. temperaturerefluxed for 30 minutes
  3. temperatureAfter refluxing for 1 hour
  4. extractionthe reaction mixture was extracted with EtOAc
  5. washwashed with concentrated HCl, water, aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. washFlash chromatography (eluting with CH2Cl2)

Sources & evidence

ORD record
ord-bd5af32121874a73a9f9f14d302437d9
Source dataset
uspto-grants-2010_05
Patent number
US07714149B2

Reaction notes

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