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Sodium Thiosulfate → Methyl 3-formyl-5-methoxybenzoate

HRID 2071071
Notes
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Reaction equation

HRID 2071071 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:2]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 15472358Methyl 3-(hydroxymethyl)-5-methoxybenzoate

Product 1

HCID 11310067Methyl 3-formyl-5-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of methyl 3-(hydroxymethyl)-5-methoxybenzoate (2.18 g, 9.82 mmol) in DCM (100 mL), Dess-Martin periodinane (5 g, 11.79 mmol) was added at rt. After 30 min stirring, the mixture was poured into a mixture of aqueous 1 M Na2S2O3 (30 mL) and aqueous saturated NaHCO3 (30 mL), and it was extracted with DCM three times. The combined organic layers were concentrated in vacuo and methyl 3-formyl-5-methoxybenzoate residue white solid (˜80% purity) was used directly for the next step reaction without further purification and identification.

Workup

  1. extractionwas extracted with DCM three times
  2. concentrationThe combined organic layers were concentrated in vacuo and methyl 3-formyl-5-methoxybenzoate residue white solid (˜80% purity)
  3. customwas used directly for the next step reaction without further purification and identification

Sources & evidence

ORD record
ord-143773716e9f4aa58096a91aa6c04e97
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08299267B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes