Acetate → 4-t-Butylazo-4-methoxypentyl chloroformate

HRID 866742Notes

Reaction equation

HRID 866742 reaction equation
[C:1]1([OH:7])C=CC=CC=1.[OH-].[K+].[C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]([N:20]=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23])(Cl)[CH3:18])(=[O:12])C.C([O-])(=O)C.C[O-].[Cl:32]C([O-])=O.C(Cl)(Cl)=O>CCCCC.N1C=CC=CC=1.CO>[Cl:32][C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]([N:20]=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23])([O:7][CH3:1])[CH3:18])=[O:12]

Participants

11

Reactant 7

HCID 175AcetateHCID 996PhenolHCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 3826051MethoxideHCID 21226386Carbonochloridate2×HCID 233459014-t-Butylazo-4-chloropentyl acetate

Product 1

HCID 203182464-t-Butylazo-4-methoxypentyl chloroformate

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 that phenol was not added to the methanolic solution of KOH before the 4-t-butylazo-4-chloropentyl acetate was added in step C. The acetate was saponified to the alcohol by addition of excess base to the methanol after the reaction of the chloro compound and the methoxide 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-0536140b539f4f48ab2927583dd906c5
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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