Water → HCID 91274406, compound

HRID 450910Notes

Reaction equation

HRID 450910 reaction equation
[CH3:1][C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:3][C:4]1[CH:5]=[C:6]([OH:14])[C:7]([CH:11]([CH3:13])[CH3:12])=[C:8]([OH:10])[CH:9]=1.C(N([CH2:26][CH3:27])CC)C.[C:28](Cl)(=[O:30])[CH3:29].[OH2:32]>ClCCl>[C:28]([O:10][C:8]1[CH:9]=[C:4]([CH:3]=[C:2]([CH3:1])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=[C:6]([O:14][C:26](=[O:32])[CH3:27])[C:7]=1[CH:11]([CH3:13])[CH3:12])(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68797239HCID 68797239, compound

Product 1

HCID 91274406HCID 91274406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(2-Methyl-2-phenylethenyl)-2-i-propyl-1,3-benzenediol (12) (3.93 mmol) and triethylamine (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 5-(2-methyl-2-phenylethenyl)-2-i-propyl-1,3-benzenediol diacetate (20).

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-efa9ae82014c4df78d1457b8f3dbfdad
Source dataset
uspto-grants-2013_07
Patent number
US08487009B2

Reaction notes

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