6-(4-Nitrophenoxy)-hexanoic acid methyl ester → 6-(4-Nitrophenoxy)hexanoic acid

HRID 1098723Notes

Reaction equation

HRID 1098723 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1>Cl>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:19])=[O:2])=[CH:15][CH:14]=1)([O-:18])=[O:17]

Participants

3

Reactant 1

HCID 146502956-(4-Nitrophenoxy)-hexanoic acid methyl ester

Product 1

HCID 223889056-(4-Nitrophenoxy)hexanoic acidYield 80.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6-(4-nitrophenoxy)-hexanoic acid methyl ester 21 (125 g, 468.16 mmol) was refluxed in conc. HCl (1250 ml) for 16 hours. The reaction mixture was cooled to room temp., filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to get pure 35 (95 g, 80.2%) as a white powder with an m.p. between 104-107° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temp.
  2. filtrationfiltered
  3. customdried
  4. customrecrystallised from a mixture of ethyl acetate:hexane (1:6)

Sources & evidence

ORD record
ord-c2a93710fe3b40efa96dbe75f64030ca
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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