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

HRID 1494230Notes

Reaction equation

HRID 1494230 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-30dd45849d2f41e888005453ea1a8781
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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