Oxalyl chloride → HCID 13923222, compound

HRID 34426Notes

Reaction equation

HRID 34426 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=O.[C:7]([C:12]1[C:13](=[O:25])[CH2:14][CH:15]([CH:19]2[CH2:24][CH2:23][CH2:22][S:21][CH2:20]2)CC=1O)(=[O:11])[CH2:8][CH2:9][CH3:10]>C(OC)(C)(C)C>[C:7]([C:12]1[C:13](=[O:25])[CH2:14][CH:15]([CH:19]2[CH2:24][CH2:23][CH2:22][S:21][CH2:20]2)[CH2:2][C:1]=1[Cl:6])(=[O:11])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 178450332HCID 178450332, compound

Product 1

HCID 13923222HCID 13923222, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

420 ml of oxalyl chloride were added at 0° to 5° C. to 141.2 g (0.5 mol) of 2-butyryl-3-hydroxy-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one, and the mixture was stirred at room temperature for 16 hours and concentrated. The oil obtained was treated with methyl tert.-butyl ether, and the resulting solid was filtered off with suction and dried. This gave 125.9 g (84% yield) of 2-butyryl-3-chloro-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one having a melting point of 97° C. (decomposition) (compound no. 312).

Workup

  1. concentrationconcentrated
  2. customThe oil obtained
  3. filtrationthe resulting solid was filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-a014d6e381fe4f1ba33060fdff7657ff
Source dataset
uspto-grants-1988_08
Patent number
US04761486

Reaction notes

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