Hydrochloric Acid → HCID 19013137, compound

HRID 1729000Notes

Reaction equation

HRID 1729000 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH2:15]([O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].CN(C1C=CC=CN=1)C.Cl>ClCCl>[CH2:15]([O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]3)=[O:29])=[CH:26][CH:25]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 855576-Hydroxy-2-naphthoic acidHCID 27602504-Octyloxybenzoyl chloride

Product 1

HCID 19013137HCID 19013137, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 ml of dichloromethane, 3 g of 6-hydroxy-2-naphthoic acid and 2.4 g oftriethylamine were dissolved. To this solution were added 4.4 g of 4-octyloxybenzoic acid chloride and 0.2 g of dimethylaminopyridine, and the solution was stirred for about 20 hours at an ambient temperature. A diluted hydrochloric acid solution was added to the solution and the organic layer in the mixed solution was separated by means of a separatingfunnel. After the solvent was distilled off, the residue was washed with n-hexane and dried to obtain 5.9 g of 6-(4-octyloxyphenylcarbonyloxy)-2-naphthoic acid. The compound was added in 10 g of thionyl chloride to dissolve, and a very small amount of N,N-dimethyl formamide was added to the solution and the solution was refluxed for 4 hours. An excess amount of thionyl chloride was distilled off to obtain 5.7 g of the titled compound.

Workup

  1. customthe organic layer in the mixed solution was separated by means of a separatingfunnel
  2. distillationAfter the solvent was distilled off
  3. washthe residue was washed with n-hexane
  4. customdried

Sources & evidence

ORD record
ord-8b5218cd00834320b287ebf85a6d801e
Source dataset
uspto-grants-1994_07
Patent number
US05330678

Reaction notes

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