Potassium Carbonate → 2-Hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester

HRID 1494228Notes

Reaction equation

HRID 1494228 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.[C:30]1([CH2:36][O:37][C:38](=[O:50])[C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([CH2:46][CH2:47][CH3:48])[C:40]=2[OH:49])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:30]1([CH2:36][O:37][C:38](=[O:50])[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:9]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:41]([CH2:46][CH2:47][CH3:48])[C:40]=2[OH:49])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149862851-(6-Iodohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 14986292HCID 14986292, compound

Product 1

HCID 149863322-Hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl esterYield 60.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.31 g (2.6 mmol) of 1-(6-iodohexyl)-2,3-bis(phenylmethoxy)benzene, 0.74 g (2.6 mmol) of 2,4-dihydroxy-3-propylbenzoic acid phenylmethyl ester and 0.54 g (3.9 mmol) of potassium carbonate in 35 mL of acetone was stirred at reflux for 39 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to an oil which was purified by HPLC using 8% ethyl acetate-hexane to give 1.03 g (60% yield) of 2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester as an oil.

Workup

  1. temperatureat reflux for 39 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure to an oil which
  4. customwas purified by HPLC

Sources & evidence

ORD record
ord-6d952af52b064b1e9dc04a77deea9308
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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