Sodium Hydroxide → HCID 17958912, compound

HRID 1156845Notes

Reaction equation

HRID 1156845 reaction equation
C([O:3][C:4]([C:6]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:8][O:7]1)=[O:5])C.[OH-].[Na+]>O1CCCC1>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]2([C:4]([OH:5])=[O:3])[CH2:8][O:7]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15291201Ethyl 2-[5-(4-chlorophenoxy)pentyl]oxirane-2-carboxylate

Product 1

HCID 17958912HCID 17958912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of 2-[5-(4-chlorophenoxy)pentyl]oxirane-2-carboxylic acid ethyl ester, 6.4 ml of 1 N sodium hydroxide solution and 6.4 ml of tetrahydrofuran are stirred at room temperature until a clear solution has formed (after about one hour). The solution is concentrated to one half of its volume in vacuo and 6.5 ml of 1 N hydrochloric acid are added while cooling with ice. The resulting mixture is extracted 3 times with 20 ml of diethyl ether each time. After drying the combined organic phases over sodium sulfate and evaporating off the solvent 1.65 g of the title compound as a viscous oil are obtained.

Workup

  1. customhas formed (after about one hour)
  2. concentrationThe solution is concentrated to one half of its volume in vacuo and 6.5 ml of 1 N hydrochloric acid
  3. additionare added
  4. temperaturewhile cooling with ice
  5. extractionThe resulting mixture is extracted 3 times with 20 ml of diethyl ether each time
  6. dry with materialAfter drying the combined organic phases over sodium sulfate
  7. customevaporating off the solvent 1.65 g of the title compound as a viscous oil
  8. customare obtained

Sources & evidence

ORD record
ord-d5106cc12588435c911b754fd7902840
Source dataset
uspto-grants-1982_06
Patent number
US04337267

Reaction notes

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