4-Methoxyphenol → HCID 20329788, compound

HRID 2058048Notes

Reaction equation

HRID 2058048 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[C:14]([O:16][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 90154-MethoxyphenolHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 18922786HCID 18922786, compound

Product 1

HCID 20329788HCID 20329788, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml of pyridine were dissolved 1 g of 7-nitro-1,2,3,4-tetrahydro-1-naphthoic acid and 560 mg of p-methoxyphenol. To the solution which had been cooled was added 700 mg of phosphorus oxychloride and the mixture was allowed to stand for 2 days. The reaction mixture was poured into ice water, made slightly alkaline with a 5% sodium hydrogen carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was separated and concentrated under reduced pressure to remove the ethyl acetate. The residue was recrystallized from an ethyl acetate-hexane mixture to obtain 0.8 g of p-methoxyphenyl 7-nitro-1,2,3,4-tetrahydro-1-naphthoate, m.p. 109°-110° C.

Workup

  1. temperatureTo the solution which had been cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. concentrationconcentrated under reduced pressure
  5. customto remove the ethyl acetate
  6. customThe residue was recrystallized from an ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-f2443f6ca8664322b17d4ca7f9677b03
Source dataset
uspto-grants-1980_07
Patent number
US04214093

Reaction notes

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