Water → HCID 66842949, compound

HRID 252316Notes

Reaction equation

HRID 252316 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([OH:19])[C:12]([CH2:16][CH2:17][CH3:18])=[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[CH2:16][CH2:17][CH3:18])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66842685HCID 66842685, compound

Product 1

HCID 66842949HCID 66842949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(2-Phenylethenyl)-2-1-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)-2-1-propylphenyl acetate. (1.32 g, 92%) as a white solid. 1HNMR (CDCl3, ppm): δ 1.26 (d, J=7.0 Hz, 6H), 2.35 (s, 6H), 3.08 (hept., J=7.0 Hz, 1H), 6.98 (d, J=17.4 Hz, 1H), 7.04 (d, J=17.4 Hz, 1H), 7.07 (s, 2H), 7.24-7.29 (m, 1H), 7.34-7.38 (m, 2H), 7.45-7.49 (m, 2H).

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-d38f06a64059409d81443ddca3d7eb70
Source dataset
uspto-grants-2011_01
Patent number
US07868047B2

Reaction notes

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