Water → HCID 54068677, compound

HRID 330339Notes

Reaction equation

HRID 330339 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([S:13][CH:14]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:15]=[C:16]([CH3:18])[CH3:17])[CH:9]=[C:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].N1[CH:38]=[CH:37]C=CC=1.[OH2:39]>>[C:26]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([S:13][CH:14]([C:19]2[CH:20]=[CH:21][C:22]([O:25][C:37](=[O:39])[CH3:38])=[CH:23][CH:24]=2)[CH:15]=[C:16]([CH3:18])[CH3:17])[CH:9]=[C:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 53702440HCID 53702440, compound

Product 1

HCID 54068677HCID 54068677, compound

Procedure

A mixture of 6.87 g (35.4 mmol) of 4-hydroxyphenyl-3-methylbut-2-enylsulfide, 12.96 g (126 mmol) of acetic anhydride and 10 ml of pyridine was heated at reflux for 1.5 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, poured into water and extracted with 2×50 ml ether. The ether extracts were combined and washed successively with water and saturated NaCl solution and then dried (MgSO4). The solution was filtered and the solvent removed in-vacuo to give the title compound as a pale yellow oil. PMR (CDCl3): δ1.55 (3H, s), 1.71 (3H, s), 2.29 (3H, s), 3.51 2H, d, J~7.6 Hz , 5.28 (1H, m), 7.00 (2H, d, J~8.8 Hz), 7 35 (2H, d, J~8.8 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours under a nitrogen atmosphere
  3. extractionextracted with 2×50 ml ether
  4. washwashed successively with water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. filtrationThe solution was filtered
  7. customthe solvent removed in-vacuo

Sources & evidence

ORD record
ord-6db135f5019a4c9caefdd9d9d75f6e2f
Source dataset
uspto-grants-1990_01
Patent number
US04895868

Reaction notes

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