HCID 23321240, compound → HCID 23321269, compound

HRID 280715Notes

Reaction equation

HRID 280715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH:11]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([S:21][CH:22]([CH3:25])[CH2:23][CH3:24])=[CH:17][CH:16]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[O-:26]I(=O)(=O)=O.[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH:11]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH:22]([CH3:25])[CH2:23][CH3:24])=[O:26])=[CH:17][CH:16]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 23321240HCID 23321240, compoundHCID 23667635Sodium periodate

Product 1

HCID 23321269HCID 23321269, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2-(4-chlorophenyl)-4-[4-(1-methylpropylthio)phenoxymethyl]-1,3-dioxolane (7.1 mmol) in 10 ml of methanol at 0° is added, dropwise over 5 min., sodium m-periodate (1.67 g, 7.8 mmol) in 13 ml of water. The mixture is stirred for 3 hours while warming to RT. The reaction mixture is poured into water and extracted with ether. The combined organic extracts are washed with saturated sodium thiosulfate, with water and with brine, dried and rotoevaporated to give 2-(4-chlorophenyl)-4-[4-(1-methylpropylsulfinyl)phenoxymethyl]-1,3-dioxolane.

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts are washed with saturated sodium thiosulfate, with water and with brine
  3. customdried

Sources & evidence

ORD record
ord-cc8d34f654314af5b5794410e912c526
Source dataset
uspto-grants-1986_05
Patent number
US04590282

Reaction notes

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