Hydrochloric Acid → 4-(2-Phenyl-chroman-6-yloxy)-cyclohexanone

HRID 59773Notes

Reaction equation

HRID 59773 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[O:18][CH:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16][CH2:15]4)[CH2:7][CH2:6]2)[O:4]CC1.Cl>O1CCCC1.C(OCC)(=O)C>[C:22]1([CH:17]2[CH2:16][CH2:15][C:14]3[C:19](=[CH:20][CH:21]=[C:12]([O:11][CH:8]4[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]4)[CH:13]=3)[O:18]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 903901236-(1,4-Dioxa-spiro[4.5]dec-8-yloxy)-2-phenyl-chroman

Product 1

HCID 903901554-(2-Phenyl-chroman-6-yloxy)-cyclohexanoneYield 94.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

430 mg of 6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-2-phenyl-chroman were dissolved at room temperature in 5 ml of tetrahydrofuran. 5 ml of 10% aqueous hydrochloric acid were added and stirring at room temperature was continued for 16 h. The reaction mixture was diluted with ethyl acetate and the organic layer washed with saturated aqueous solution of sodium hydrogencarbonate. The organic layer was dried with sodium sulfate and filtered, and the volatile components removed under reduced pressure. 357 mg of the title compound were obtained as a pale yellow solid.

Workup

  1. washthe organic layer washed with saturated aqueous solution of sodium hydrogencarbonate
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. customthe volatile components removed under reduced pressure

Sources & evidence

ORD record
ord-95dbefce21d34803ba6c07ab62feab17
Source dataset
uspto-grants-2016_09
Patent number
US09440941B2

Reaction notes

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