Phosgene → Benzoyl chloride, 3,4,5-trimethoxy-

HRID 1657936Notes

Reaction equation

HRID 1657936 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](O)=[O:7].CP(=O)(C)CCCCCCCCCCCC.C(Cl)([Cl:34])=O>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:34])=[O:7]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 83573,4,5-Trimethoxybenzoic AcidHCID 13380Phosphine oxide, dodecyldimethyl-

Product 1

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 100 g of 3,4,5-trimethoxybenzoic acid, 150 g of xylene and 0.1 g of dimethyl-dodecyl-phosphine oxide is treated with phosgene at 100°C in the apparatus described for example 1. After a lapse of abt. 1 hour and phosgene consumption of 140 g the absorption of phosgene is terminated. At the end of a two-hours-postreaction a yellow solution of 3,4,5-trimethoxy-benzoylchloride is obtained. The yield in dissolved acid chloride is approx. 106 g, corresponding to 97.5% of the theoretical yield, calculated on the acid used. The solution may be used directly for further reactions after having eliminated the remaining phosgene by means of nitrogen or by distillation of a part of the solvent. But it is also possible to isolate the trimethoxy-benzoylchloride in its pure form by means of vacuum distillation (boiling point: 137°C/1.5 torr. softening point: 80 to 81°C).

Workup

  1. custom1 hour and phosgene consumption of 140 g
  2. customthe absorption of phosgene
  3. customis terminated

Sources & evidence

ORD record
ord-636f235f870f418cac0a29742cce9651
Source dataset
uspto-grants-1976_06
Patent number
US03962326

Reaction notes

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