Benzoic Acid → ON-013100

HRID 424357Notes

Reaction equation

HRID 424357 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:5][S:6]([CH2:9][C:10](O)=O)(=[O:8])=[O:7].[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[C:21]=1C=O.C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:29][O:28][C:26]1[CH:25]=[C:24]([O:30][CH3:31])[CH:21]=[C:20]([O:19][CH3:18])[C:27]=1/[CH:10]=[CH:9]/[S:6]([CH2:5][C:4]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:2]([OH:1])[CH:3]=1)(=[O:8])=[O:7]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 700192,4,6-TrimethoxybenzaldehydeHCID 11357417HCID 11357417, compound

Product 1

HCID 11269418ON-013100Yield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the 2-((3-hydroxy-4-methoxybenzyl)sulfonyl)acetic acid (1.9 g, 7.3 mmol, 1 eq), 2,4,6-trimethoxybenzaldehyde (1.58 g, 8.0 mmol, 1.1 eq.), benzoic acid (134 mg, 0.15 eq.) and piperidine (81 mg, 0.13 eq.) in toluene (50 mL) was heated at reflux temperature for 2-3 h with continuous removal of water using a Dean-Stark trap. When the reaction was complete by TLC analysis, the reaction mixture was cooled to room temperature. Water was added and the resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic extract was washed with saturated aqueous sodium bicarbonate solution (50 mL), dilute hydrochloric acid (50 mL), and water (50 mL) and dried (sodium sulfate). Volatile components were removed in vacuo to yield the crude product, which was purified by recrystallization from isopropanol to yield 1.8 g (62.5%) of the desired (E)-5-((2,4,6-trimethoxystyryl-sulfonyl)methyl)-2-methoxyphenol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2-3 h
  3. customwith continuous removal of water using a Dean-Stark trap
  4. additionWater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
  6. extractionThe combined organic extract
  7. washwas washed with saturated aqueous sodium bicarbonate solution (50 mL), dilute hydrochloric acid (50 mL), and water (50 mL)
  8. dry with materialdried (sodium sulfate)
  9. customVolatile components were removed in vacuo
  10. customto yield the crude product, which
  11. customwas purified by recrystallization from isopropanol

Sources & evidence

ORD record
ord-60944c59e79446039e45c3efd8ffe6c9
Source dataset
uspto-grants-2012_01
Patent number
US08106033B2

Reaction notes

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