Hydrochloric Acid → HCID 19088052, compound

HRID 1646823Notes

Reaction equation

HRID 1646823 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)=[O:6].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([C:28]1[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[C:30]([CH3:38])[C:29]=1[O:39][CH3:40])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>CN(C)C=O>[CH3:40][O:39][C:29]1[C:30]([CH3:38])=[C:31]([CH3:37])[C:32]([O:35][CH3:36])=[C:33]([CH3:34])[C:28]=1[CH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([O:4][CH3:3])=[O:6])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7456MethylparabenHCID 24758Sodium hydrideHCID 19088033HCID 19088033, compound

Product 1

HCID 19088052HCID 19088052, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A 0.42 g (10×1.05 mmole) quantity of sodium hydride (60%, oily preparation) was added to a solution of 1.52 g (10.0 mmole) of methyl p-hydroxybenzoate in dimethylformamide (15 ml) under ice-cooling, followed by stirring for 5 minutes. The cooling bath was removed, and a solution of 4.80 g (10.0 mmole) of 1-iodo-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptane in dimethylformamide (15 ml) was added to the mixture. Then, the temperature was raised to 50° C., and stirring was effected for 1 hour. After ice-cooling, dilute hydrochloric acid was added to suspend the reaction, and the product was extracted with isopropyl ether. The isopropyl ether layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residual solution was chromatographed on a silica gel column to perform purification (elution with hexane/isopropyl ether) to thereby give 4.95 g (98%) of methyl 4-[7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptoxy]benzoate. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 14.

Workup

  1. temperaturecooling
  2. customThe cooling bath was removed
  3. stirringstirring
  4. waitwas effected for 1 hour
  5. temperatureAfter ice-cooling
  6. customthe reaction
  7. extractionthe product was extracted with isopropyl ether
  8. customThe isopropyl ether layer was separated out
  9. washwashed with aqueous sodium chloride solution
  10. dry with materialdried (magnesium sulfate)
  11. customevaporated
  12. customThe residual solution was chromatographed on a silica gel column
  13. custompurification (elution with hexane/isopropyl ether)

Sources & evidence

ORD record
ord-f55cef6d102244ac9d2c492d97c0bb01
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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