Hydrochloric Acid → HCID 19375823, compound

HRID 2211370Notes

Reaction equation

HRID 2211370 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8](C)[CH2:9][CH2:10][C:11]([O:13]C)=O)[CH:5]=[CH:6][CH:7]=1.[CH3:16][NH:17][CH3:18].Cl>O>[CH3:16][N:17]([CH3:18])[C:11](=[O:13])[CH2:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 19375782HCID 19375782, compound

Product 1

HCID 19375823HCID 19375823, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.7 g of methyl 4-(3-hydroxyphenyl)pentanoate and 40 mL of 40% dimethylamine in water was stirred for 25 hours. The mixture was acidified with 5N hydrochloric acid and extracted with dichloromethane. The organic phase was washed with a saturated sodium chloride solution, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl ether/methanol to provide 1.62 g (41%) of the title intermediate. NMR

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed with a saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl ether/methanol

Sources & evidence

ORD record
ord-603d26c20918465396bd2f8107530252
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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