Acetone → Sodium 2-(5-phenylpentyl)oxirane-2-carboxylate

HRID 2285751Notes

Reaction equation

HRID 2285751 reaction equation
[OH-].[Na+:2].C([O:5][C:6]([C:8]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][O:9]1)=[O:7])C.CC(C)=O>O1CCCC1>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]2([C:6]([O-:7])=[O:5])[CH2:10][O:9]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1.[Na+:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 54216Ethyl 2-(5-phenylpentyl)oxirane-2-carboxylate

Product 1

HCID 23676476Sodium 2-(5-phenylpentyl)oxirane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 166 ml of 1 N sodium hydroxide solution and 90 ml of tetrahydrofuran is added dropwise to a solution of 43.6 g of 2-(5-phenylpentyl)oxirane 2-carboxylic acid ethyl ester in 90 ml of tetrahydrofuran. When the addition has ended, the mixture is stirred for about 45 minutes, until a clear solution has formed. 1.6 l of acetone are now added dropwise in the course of 3 hours, a crystalline precipitate, which is filtered off and washed with acetone, separating out. The product is recrystallized from water to give 42.9 g of the title compound as the dihydrate of m.p. 82° to 86° C.

Workup

  1. additionWhen the addition
  2. customhas formed
  3. filtrationa crystalline precipitate, which is filtered off
  4. washwashed with acetone
  5. customseparating out
  6. customThe product is recrystallized from water

Sources & evidence

ORD record
ord-e6e91e5ea71a45678736fa088eae9585
Source dataset
uspto-grants-1982_04
Patent number
US04324796

Reaction notes

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