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

HRID 1639028Notes

Reaction equation

HRID 1639028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[O:14])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C[Si](C)(C)Cl.[C:20](=[O:23])(O)[O-].[Na+].[CH3:25]N(C)C>C(O)CO>[Cl:1][C:2]1[CH:11]=[C:6]([CH:7]2[O:8][CH2:25][CH2:10][O:9]2)[C:5]([OH:12])=[C:4]([CH:3]=1)[C:13]([O:23][CH3:20])=[O:14]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 13146779Methyl 5-chloro-3-formyl-2-hydroxybenzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of methyl 5-chloro-3-formyl-2-hydroxybenzoate (73.2 g), ethylene glycol (350 ml) and trimethylchlorosilane (129 ml) 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 extracted is washed with water, dried and concentrated to remove solvent, whereby methyl 5-chloro-3-(1,3-dioxolan-2-yl)-2-hydroxybenzoate (86 g) is obtained as yellow powder.

Workup

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

Sources & evidence

ORD record
ord-c6f6f9d33c09402980128e8d2822f939
Source dataset
uspto-grants-1989_11
Patent number
US04882340

Reaction notes

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