Water → HCID 11817878, compound

HRID 1388810Notes

Reaction equation

HRID 1388810 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([SH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[O:15]1[C@H:17]2[CH2:18][C@H:19]([C:22]([CH3:24])=[CH2:23])[CH2:20][CH2:21][C@@:16]12[CH3:25]>C1(C)C=CC=CC=1.CN(C)C=O>[C:7]1([S:13][C@H:17]2[CH2:18][C@H:19]([C:22]([CH3:24])=[CH2:23])[CH2:20][CH2:21][C@@:16]2([OH:15])[CH3:25])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 6857487cis-(+)-Limonene oxide

Product 1

HCID 11817878HCID 11817878, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 164 g (1 M) of the above diastereomeric mixture, 83 g of potassium carbonate and 60.5 g (0.556 M) of thiophenol in a mixture of 380 ml of toluene and 20 ml of dimethylformamide was heated under reflux for 10 hours. After cooling to room temperature and addition of water, the separated organic layer was successively washed with water and with brine, dried over sodium sulfate and evaporated. After distillation in a bulb apparatus, the desired thioether (131 g; ca. 100% yield) was separated from unreacted (+)-(1R,2S,4R)-1,2-epoxy-8-p-menthene. The title compound thus prepared was characterized as follows:

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. washthe separated organic layer was successively washed with water and with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. distillationAfter distillation in a bulb apparatus

Sources & evidence

ORD record
ord-e3fb2617bab94f90af274fea2a3ed29c
Source dataset
uspto-grants-1984_02
Patent number
US04433183

Reaction notes

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