Acetaminophen → HCID 54064637, compound

HRID 1982181Notes

Reaction equation

HRID 1982181 reaction equation
[CH3:1][C:2]([CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH:13]=[CH:14][C:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]=1[CH3:23])=[CH:3][CH:4]=[CH:5][C:6]([OH:8])=[O:7].[C:25]([NH:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)(=[O:27])[CH3:26].FC(F)(F)C([O-])=O>O1CCCC1>[CH3:1][C:2]([CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH:13]=[CH:14][C:15]1[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]=1[CH3:23])=[CH:3][CH:4]=[CH:5][C:6]([O:8][C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:25](=[O:27])[CH3:26])=[CH:30][CH:31]=1)=[O:7]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 84468TrifluoroacetateHCID 53743104HCID 53743104, compound

Product 1

HCID 54064637HCID 54064637, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5,9-dimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoic acid (0.5 g. 1.5 mmol) and 4-acetamidophenol (1.2 g, 8 mmol) in 40 ml of tetrahydrofuran (THF) was stirred in an ice bath under nitrogen and a solution of trifluroacetate (1.4 ml) in 5 ml of THF was added dropwise. The mixture was stirred at room temperature for 24 hours and concentrated in vacuo. The residue was diluted with methylene chloride and washed with aqueous NaHCO3 solution and brine. After drying with Na2SO4, the organic solution was concentrated in vacuo to give orange powders. Crystallization from ethyl acetate afforded 0.55 g. of the title compound as orange colored crystals. mp 219°-222° C., MS (EI): 459 (m+), 309, 291, 109; UV(MeOH) λmax. 394 nm, 245 nm.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with methylene chloride
  3. washwashed with aqueous NaHCO3 solution and brine
  4. dry with materialAfter drying with Na2SO4
  5. concentrationthe organic solution was concentrated in vacuo
  6. customto give orange powders
  7. customCrystallization from ethyl acetate
  8. customafforded 0.55 g

Sources & evidence

ORD record
ord-5f31f16173c2439eb7282149766bd71b
Source dataset
uspto-grants-1986_06
Patent number
US04595696

Reaction notes

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