Hydrochloric Acid → 4-[4-(8-Methoxyoctyloxy)phenyl]benzoic acid

HRID 1872377Notes

Reaction equation

HRID 1872377 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.O.[C:27](OCC)(=[O:29])C.Cl>C[O-].[Na+].CN(C)C=O>[CH3:27][O:29][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 211822604-[4-(8-Bromooctyloxy)phenyl]benzoic acid

Product 1

HCID 211825084-[4-(8-Methoxyoctyloxy)phenyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A solution of 4-[4-(8-Bromooctyloxy)phenyl]benzoic acid (1 g) in a mixture of sodium methylate (28% solution in metanol) (10 ml) and N,N-dimethylformamide (5 ml) was refluxed for 5 hours. The reaction mixture was added to a mixture of water and ethyl acetate and adjusted to pH 2.0 with conc. HCl. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 4-[4-(8-Methoxyoctyloxy)phenyl]benzoic acid (0.77 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1ead5803961a4a638b154019ef72e94d
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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