Potassium Carbonate → HCID 54194410, compound

HRID 1492844Notes

Reaction equation

HRID 1492844 reaction equation
COC(=O)C1C=C(O)C=C(O)C=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][O:20][C:21](=[O:66])[C:22]1[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:35][CH:34]=2)[CH:25]=[C:24]([O:47]CCCOC2C=CC(OCC3C=CC=CC=3)=CC=2)[CH:23]=1>CC(C)=O.CN(C=O)C>[CH3:19][O:20][C:21](=[O:66])[C:22]1[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:35][CH:34]=2)[CH:25]=[C:24]([OH:47])[CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 54529309HCID 54529309, compound

Product 1

HCID 54194410HCID 54194410, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g (11.9 mmol) of 3,5-dihydroxybenzoic acid methyl ester, 3.8 g (11.9 mmol) of 3-[(4-phenylmethoxy)phenoxy]propyl bromide and 1.7 g (12.3 mmol) of potassium carbonate in 40 ml of acetone and 2 ml of DMF was stirred at reflux for 24 hours. The solvents were removed at reduced pressure, the residue was stirred with methylene chloride and filtered. The filtrate was concentrated to a solid which was recrystallized from methylene chloride-methanol to give 1.77 g, mp 134°-136°, of 3,5-bis[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid methyl ester. The filtrate was concentrated to a solid which was purified by chromatography on 20 g of silica gel (230-400 mesh) using 10% ethyl acetate-hexane to give 1.47 g (30% yield, mp 120°-122°) of 3-hydroxy-5-[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvents were removed at reduced pressure
  3. stirringthe residue was stirred with methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to a solid which
  6. customwas recrystallized from methylene chloride-methanol
  7. customto give 1.77 g, mp 134°-136°
  8. concentrationThe filtrate was concentrated to a solid which
  9. customwas purified by chromatography on 20 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-4bdfcfefcd3b4cfa9079f2678a61b34b
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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