2-Benzyloxyphenol → HCID 66894914, compound

HRID 19245

Reaction equation

HRID 19245 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:22]([O:24][C:25](=[O:30])[CH:26]=[C:27](Cl)[CH3:28])[CH3:23]>O1CCCC1>[CH2:22]([O:24][C:25](=[O:30])/[CH:26]=[C:27](/[O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)\[CH3:28])[CH3:23]

Participants

5

Reactant 3

HCID 804592-BenzyloxyphenolHCID 2828353-Chloro-but-2-enoic acid ethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 66894914HCID 66894914, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

Potassium t-butoxide (5.60 g, 0.05 mol) was added to a stirred solution of 2-benzyloxy-phenol (5.00 g, 0.025 mol) in tetrahydrofuran (50 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191, 3.70 g, 0.025 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-(2-benzyloxy-phenoxy)-but-2-enoic acid ethyl ester (5.70 g, 73%) as a yellow oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 0.75 h
  3. temperatureThe reaction mixture was refluxed for an additional 3 h
  4. concentrationAfter this time, the mixture was concentrated in vacuo
  5. additionthe residue was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe organic layer was then washed with 5% aqueous sodium hydroxide solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdc7cce75ed845c496478ac8e38edcf1
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Linked notes

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