Ethylene Glycol → Methyl 5-chloro-3-(1,3-dioxolan-2-yl)-2-hydroxybenzoate

HRID 1761922Notes

Reaction equation

HRID 1761922 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C[Si](C)(C)Cl.[C:19](=O)(O)[O-].[Na+].CN(C)C.[CH2:28]([OH:31])[CH2:29]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]2[O:31][CH2:28][CH2:29][O:13]2)[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 1146TrimethylamineHCID 6397ChlorotrimethylsilaneHCID 1833565-Chloro-3-formyl-2-hydroxybenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 19840310Methyl 5-chloro-3-(1,3-dioxolan-2-yl)-2-hydroxybenzoate

Procedure

A mixture of 73.2 g of 5-chloro-3-formyl-2-hydroxybenzoic acid, 350 ml of ethylene glycol and 129 ml of trimethylchlorosilane is stirred at room temperature for 2 hours. The reaction mixture is poured into a mixture of an aqueous saturated sodium bicarbonate solution and trimethylamine, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent to give 86 g of methyl 5-chloro-3-(1,3-dioxolan-2-yl)-2-hydroxybenzoate as yellow powder.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. customevaporated
  5. customto remove solvent

Sources & evidence

ORD record
ord-a37270dc9ce9443c9152c047a73c9e77
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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