Benzaldehyde → Chloro(phenyl)methyl carbonochloridate

HRID 65514Notes

Reaction equation

C(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:15][C:16]([O:18][C:19]([Cl:22])(Cl)Cl)=[O:17]>>[Cl:15][C:16]([O:18][CH:19]([Cl:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:17]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 1049Pyridine

HCID 10426Diphosgene

Product 1

HCID 14320655Chloro(phenyl)methyl carbonochloridate

Procedure

7.5 g (0.07 mole) benzaldehyde and 0.3 g (0.004 mole) pyridine are introduced in an apparatus similar to that of example 1. The mixture is brought to 45° C. and 8.5 g (0.043 mole) trichloromethyl chloroformate added drop by drop over 10 minutes. After 2 hours of stirring at 45° it is confirmed by NMR analysis that all the aldehyde has been converted to the α-chlorinated chloroformate with formula: ##STR7##

Workup

customis brought to 45° C.

Sources & evidence

ORD record: ord-f30aceb902644849b20934c8cab3aec1
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04614829

Reaction notes

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