Water → HCID 66842769, compound

HRID 2252342Notes

Reaction equation

HRID 2252342 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([OH:19])[C:12]([CH:16]([CH3:18])[CH3:17])=[C:13]([OH:15])[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N([CH2:25][CH3:26])CC)C.[C:27](Cl)(=[O:29])[CH3:28].[OH2:31]>ClCCl>[C:27]([O:19][C:11]1[CH:10]=[C:9]([CH:8]=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:14]=[C:13]([O:15][C:25](=[O:31])[CH3:26])[C:12]=1[CH:16]([CH3:17])[CH3:18])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 133191HCID 133191, compound

Product 1

HCID 66842769HCID 66842769, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(2-Phenylethenyl)-2-i-propyl-1,3-benzenediol obtained in example 11 (1.00 g, 3.93 mmol) and triethylamine (1.5 mL, 10.8 mmol) in dichloromethane (100 mL) at 0° C. was added acetyl chloride dropwise. The reaction was monitored by TLC. Water (50 mL) was added after the reaction was complete (˜30 min.). The organic layer was separated and washed with 2NHCl (30 mL), H2O (50 mL), saturated NaHCO3 (50 mL), H2O (50 mL) and brine (50 mL), and dried over anhydrous sodium sulfate. Evaporation of the solution followed by flash chromatography using 5% ethyl acetate in hexane yielded 3-acetoxy-5-(2-phenylethenyl)-2-i-propylphenyl acetate. (1.32 g, 92%) as a white solid.

Workup

  1. custom(˜30 min.)
  2. customThe organic layer was separated
  3. washwashed with 2NHCl (30 mL), H2O (50 mL), saturated NaHCO3 (50 mL), H2O (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solution

Sources & evidence

ORD record
ord-4570722be4b7418599277d73667e5346
Source dataset
uspto-grants-2008_01
Patent number
US07321050B2

Reaction notes

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