Hydrochloric Acid → HCID 67415126, compound

HRID 708305Notes

Reaction equation

HRID 708305 reaction equation
COC[O:4][C:5]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:6]=1[CH:7]=[O:8].C[C:15]1[CH:22]=[CH:21][CH:20]=[C:19](C)[C:16]=1[CH:17]=O.Cl>O1CCCC1>[C:5]1([C:17]([C:16]2[CH:15]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:17][C:16]2[CH:19]=[CH:20][C:21]([C:7]([C:6]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:5]=3[OH:4])=[O:8])=[CH:22][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5838412,6-DimethylbenzaldehydeHCID 122175302-(Methoxymethoxy)-5-methylbenzaldehyde

Product 1

HCID 67415126HCID 67415126, compoundYield 211.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

An intermediate compound was prepared by the same method described in Example 6 except that 2-methoxymethoxy-5-methylbenzaldehyde (1.3 g) synthesized in the above-described Synthesis Example 3 was used instead of 2,6-dimethylbenzaldehyde (0.65 g). A 6 N hydrochloric acid solution (1 mL) was added to a tetrahydrofuran solution (30 mL) of the intermediate compound, 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 2.0 g (yield: 84%) of [4-(2,2-diphenylvinyl)phenyl]-(2-hydroxy-5-methylphenyl)methanone (12) as white crystals. The structure of Product 12 was confirmed by 1H-NMR. Table 1 shows optical characteristics and practical utility of Product 12.

Workup

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

Sources & evidence

ORD record
ord-39a85f4e409f4936a9a18d6d08f4316a
Source dataset
uspto-grants-2015_11
Patent number
US09176257B2

Reaction notes

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