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1,5-Bis(4-methoxymethoxy-3-methoxyphenyl)-1,4-pentadien-3-one → 1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

HRID 77649
Notes
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Reaction equation

HRID 77649 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:28])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22]COC)=[C:18]([O:26][CH3:27])[CH:17]=2)=[CH:7][C:6]=1[O:29][CH3:30]>CO.Cl>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([CH:15]=[CH:14][C:13](=[O:28])[CH:12]=[CH:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[C:6]([O:29][CH3:30])[CH:7]=2)=[CH:17][C:18]=1[O:26][CH3:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 695016911,5-Bis(4-methoxymethoxy-3-methoxyphenyl)-1,4-pentadien-3-one

Product 1

HCID 4681331,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-oneYield 96%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1,5-Bis(4-methoxymethoxy-3-methoxyphenyl)-1,4-pentadien-3-one (20j, 0.41 g, 10.0 mmol) was stirred in methanol (50 ml) for 15 min at 50° C. Concentrated hydrochloric acid (1 drop) was added and the solution stirred for 3 hr at 50° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a semi-solid. The crude semi-solid was purified by preparative thin layer chromatography with ethyl acetate/hexane to give 0.31 g (96%) of a yellow solid: mp 84-86° C. [expected mp 82-83° C.]; 1H NMR: δ 3.89 (s, 6H), 6.87 (d, 2H, J=8.4 Hz), 6.88 (d, 2H, J=15.9 Hz), 7.10 (m, 4H), 7.62 (d, 2H, J=15.9 Hz); 13C NMR: δ 56.1, 109.8, 114.8, 123.3, 123.4, 127.5, 143.0, 146.8, 148.1, 188.6.

Workup

  1. customThe methanol was evaporated
  2. extractionthe resulting residue extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a semi-solid
  8. customThe crude semi-solid was purified by preparative thin layer chromatography with ethyl acetate/hexane

Sources & evidence

ORD record
ord-ea92152f73f6479ab7d3bb92e858f885
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841326B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes