Acetate → HCID 86735853, compound

HRID 866741Notes

Reaction equation

HRID 866741 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:12]1([OH:18])C=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+].C([O-])(=O)C.[Cl:25][C:26]([O-])=[O:27].C(Cl)(Cl)=O>CCCCC.N1C=CC=CC=1.CO>[Cl:25][C:26]([O:18][CH2:12][CH2:13][CH2:14][CH:15]([S:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)[CH3:16])=[O:27]

Participants

10

Reactant 6

HCID 175AcetateHCID 996PhenolHCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 754544-Tert-Butylbenzenethiol2×HCID 21226386Carbonochloridate2×

Product 1

HCID 86735853HCID 86735853, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8003PentaneSolvent2×

Procedure

This compound was prepared in the same manner as the 4-phenoxy derivative described in Example XXIX except p-t-butylthiophenol was added instead of phenol to the methanolic solution of KOH before the chloro compound was added in step C. The acetate was saponified to the alcohol by the addition of excess base to the methanol after the reaction of the chloro compound and the p-t-butylthiophenol was complete. The alcohol was then converted to the chloroformate by adding a pentane solution of the alcohol and pyridine to a pentane solution of phosgene as in step D of Example XXIX. The infrared spectrum confirmed that the alcohol was converted to the chloroformate.

Workup

  1. additionwas added in step C

Sources & evidence

ORD record
ord-8b13ca1dd39545948405a4218acbc83a
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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