Water → 1,5-Bis(4-acetoxyphenyl)-1,4-pentadien-3-one

HRID 77668Notes

Reaction equation

HRID 77668 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].N1[CH:33]=[CH:32]C=CC=1.[OH2:34]>>[C:21]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][C:32](=[O:34])[CH3:33])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1074411,5-Bis(4-hydroxyphenyl)-1,4-pentadien-3-one

Product 1

HCID 690190861,5-Bis(4-acetoxyphenyl)-1,4-pentadien-3-oneYield 82%

Procedure

1,5-Bis(4-hydroxyphenyl)-1,4-pentadien-3-one (20f, 0.26 g, 1.0 mmol) was dissolved in acetic anhydride (21, 7.00 ml, 74.1 mmol) and stirred for 5 min at room temperature. Pyridine (0.70 ml, 8.7 mmol) was added and the mixture stirred for 30 min at 100° C. The resulting mixture was poured into water, extracted with ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from tetrahydrofuran/hexane to give 0.28 g (82%) of a yellow solid: mp 167-168° C. [expected mp 167-168° C.]; 1H NMR: δ 2.30 (s, 6H), 7.00 (d, 2H, J=15.9 Hz), 7.13 (d, 4H, J=8.3 Hz), 7.60 (d, 4H, J=8.2 Hz), 7.69 (d, 2H, J=15.9 Hz); 13C NMR: δ 21.1, 122.1, 125.4, 129.4, 132.4, 142.1, 152.2, 168.9, 188.3; Exact mass calcd for C21H18O5: 350.1154, observed (M+H) 351.1232.

Workup

  1. stirringthe mixture stirred for 30 min at 100° C
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-8739ff5e39b7463c8e139d1193400580
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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