Hydrochloric Acid → HCID 54508794, compound

HRID 846486Notes

Reaction equation

HRID 846486 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[C:16]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:19]=[CH:18][C:17]=1[O:28]C>N1C=CC=CC=1>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][C:5]=1[C:16]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:19]=[CH:18][C:17]=1[OH:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9952142HCID 9952142, compound

Product 1

HCID 54508794HCID 54508794, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of pyridine (30 ml) and conc. hydrochloric acid (30 ml) was heated at about 180° C. for 30 mins. A known compound, 2,2'-dimethoxy-5,5'-bis (3-carboxypropyl) biphenyl (1.2 g) was added thereto and the mixture was heated at about 180° C. with stirring overnight. Upon cooling, the reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate under acidic conditions with hydrochloric acid. The ethyl acetate layer was washed with aqueous saturated sodium chloride, dried by adding anhydrous magnesium sulfate, then the solvent was evaporated off under reduced pressure. A residue was re-precipitated by adding ethyl acetate-toluene to obtain 2,2'-dihydroxy-5,5'-bis (3-carboxypropyl) biphenyl (1.01 g, 91%) as a white powder. 1H-NMR (CD3OD) δ (ppm): 1.8-2.1 (4H, m, 2CH2), 2.32 (4H, t, 2CH2), 2.63 (4H, t, 2CH2), 6.84 (2 H, d, arom-H), 6.9-7.2 (4H, m, arom-H) MS (FAB): 357 (M-H)-

Workup

  1. temperaturethe mixture was heated at about 180° C.
  2. temperatureUpon cooling
  3. extractionthe mixture was extracted with ethyl acetate under acidic conditions with hydrochloric acid
  4. washThe ethyl acetate layer was washed with aqueous saturated sodium chloride
  5. customdried
  6. additionby adding anhydrous magnesium sulfate
  7. customthe solvent was evaporated off under reduced pressure
  8. customA residue was re-precipitated
  9. additionby adding ethyl acetate-toluene

Sources & evidence

ORD record
ord-3725ba4605c94068a8c4d957f4aa4c93
Source dataset
uspto-grants-1992_08
Patent number
US05136090

Reaction notes

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