Acetone → 5-Chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid methyl ester

HRID 1613058Notes

Reaction equation

HRID 1613058 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH3:30][O:31][C:32](=[O:45])[C:33]1[CH:38]=[C:37]([Cl:39])[C:36]([OH:40])=[CH:35][C:34]=1CC(O)C.C(=O)([O-])[O-:47].[K+].[K+].[CH3:52][C:53]([CH3:55])=O>>[CH3:30][O:31][C:32](=[O:45])[C:33]1[CH:38]=[C:37]([Cl:39])[C:36]([O:40][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:35]([CH2:52][CH2:53][CH3:55])[C:34]=1[OH:47]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 149862851-(6-Iodohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 678827165-Chloro-2,4-dihydroxypropylbenzoic acid methyl ester

Product 1

HCID 149863355-Chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid methyl esterYield 68%

Procedure

A mixture of 0.41 g (0.8 mmol) of 1-(6-iodohexyl)-2,3-bis(phenylmethoxy)benzene, 0.18 g (0.74 mmol) of 5-chloro-2,4-dihydroxypropylbenzoic acid methyl ester and 0.22 g (1.6 mmol) of potassium carbonate in 15 mL of acetone was stirred at reflux for 16 hours. The reaction mixture was filtered and the filtrate was concentrated to an oil. Chromatography on 30 g of silica gel and elution with 10% ethyl acetate-hexane gave 0.31 g (68% yield) of 5-chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to an oil
  4. washChromatography on 30 g of silica gel and elution with 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-f7160014593d4e6ca93d076753ba81bc
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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