Hydrochloric Acid → HCID 13309739, compound

HRID 1903889Notes

Reaction equation

HRID 1903889 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]([OH:21])([CH2:16][CH2:17][C:18]([CH3:20])=[CH2:19])[C:14]#[N:15].Cl>C(Cl)Cl>[OH:9][CH2:19][C:18]1([CH3:20])[O:21][C:13]([CH3:12])([C:14]#[N:15])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70297m-Chloroperbenzoic acidHCID 20432101HCID 20432101, compound

Product 1

HCID 13309739HCID 13309739, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (ice bath) and stirred mixture of 139.52 g 86% m-chloroperbenzoic acid in 2 liters methylene chloride was added 87.98 g of crude 2,5-dimethyl-2-hydroxy-5-hexenenitrile. After 30 minutes at 3° C., the mixture was allowed to warm to room temperature (ca 25° C.). The resulting mixture, which contained the intermediate epoxy cyanohydrin, was then treated with 790 ml of 0.12 N hydrochloric acid to effect cyclization. After stirring vigorously for an additional 2 hours at ca 25° C., the organic phase was separated, washed with 10% aqueous sodium carbonate and dried (MgSO4). Evaporation of solvent and distillation of the residue afforded 62.87 g product with bp 100°-105° C. (0.3 torr).

Workup

  1. temperatureTo a cooled (ice bath)
  2. stirringAfter stirring vigorously for an additional 2 hours at ca 25° C.
  3. customthe organic phase was separated
  4. washwashed with 10% aqueous sodium carbonate
  5. dry with materialdried (MgSO4)
  6. customEvaporation of solvent and distillation of the residue

Sources & evidence

ORD record
ord-f6482b1fde114165a57b2bf9044e4fb9
Source dataset
uspto-grants-1984_03
Patent number
US04439225

Reaction notes

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