Hydrochloric Acid → 3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one

HRID 536999Notes

Reaction equation

HRID 536999 reaction equation
C([O:3][C:4]1(OCC)[CH2:11][C:10]2[C:5]1=[CH:6][C:7]([O:14][CH3:15])=[C:8]([O:12][CH3:13])[CH:9]=2)C.Cl.O>C1COCC1.O>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:14][CH3:15])[C:4](=[O:3])[CH2:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 1176363657,7-Diethoxy-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene

Product 1

HCID 27527583,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-oneYield 81.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

7,7-Diethoxy-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene (1.76 g, 6.98 mmol) is stirred in a mixture of THF/water (6/1) at ambient temperature. 815 mg of an aqueous 11N HCl solution (1.1 eq, 7.7 mmol) are then added. The reaction mixture is stirred for 2 hours ambient temperature. Water is added to facilitate two extractions with ethyl acetate (2×30 mL). The organic phases are dried over MgSO4 and then subjected to drying. There are obtained 1.01 g of the title product in the form of a grey powder.

Workup

  1. extractiontwo extractions with ethyl acetate (2×30 mL)
  2. dry with materialThe organic phases are dried over MgSO4
  3. customto drying

Sources & evidence

ORD record
ord-a55c9872dcac49f7952bb584fe88330a
Source dataset
uspto-grants-2014_10
Patent number
US08859763B1

Reaction notes

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