Hydrochloric Acid → [4-(2,2-Diphenylvinyl)phenyl]-(2-hydroxyphenyl)methanone

HRID 708304Notes

Reaction equation

HRID 708304 reaction equation
COC[O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].C[C:14]1[CH:21]=[CH:20][CH:19]=[C:18](C)[C:15]=1[CH:16]=O.Cl>O1CCCC1>[C:5]1([C:16]([C:15]2[CH:14]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:16][C:15]2[CH:18]=[CH:19][C:20]([C:7]([C:6]3[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=3[OH:4])=[O:8])=[CH:21][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5838412,6-DimethylbenzaldehydeHCID 108774852-(Methoxymethoxy)benzaldehyde

Product 1

HCID 67415935[4-(2,2-Diphenylvinyl)phenyl]-(2-hydroxyphenyl)methanoneYield 208.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A tetrahydrofuran solution (30 mL) of the intermediate compound was prepared by the same method described in Example 6 except that 2-methoxymethoxybenzaldehyde (1.2 g) synthesized in the above-described Synthesis Example 2 was used instead of 2,6-dimethylbenzaldehyde (0.65 g). A 6 N hydrochloric acid solution (1 mL) was added to the tetrahydrofuran solution, and the mixture was stirred at 25° C. for 12 hours. After confirmation of the degree of reaction progress by TLC, the reaction was quenched with an aqueous solution of sodium hydrogen carbonate, and the organic phase was extracted with ethyl acetate. The resulting organic phase was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to obtain 1.9 g (yield: 84%) of [4-(2,2-diphenylvinyl)phenyl]-(2-hydroxyphenyl)methanone (10) as yellow crystals. The structure of Product 10 was confirmed by 1H-NMR. Table 1 shows optical characteristics and practical utility of Product 10.

Workup

  1. customsynthesized in the above-described Synthesis Example 2
  2. customAfter confirmation of the degree of reaction progress by TLC
  3. customthe reaction was quenched with an aqueous solution of sodium hydrogen carbonate
  4. extractionthe organic phase was extracted with ethyl acetate
  5. dry with materialThe resulting organic phase was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customrecrystallized

Sources & evidence

ORD record
ord-b23a58b35a534179bdcc55c2b6d057da
Source dataset
uspto-grants-2015_11
Patent number
US09176257B2

Reaction notes

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