Sodium Thiosulfate → Methyl 2-(4-formylphenyl)acetate

HRID 1612411Notes

Reaction equation

HRID 1612411 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25](=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.CCOCC.C(=O)(O)[O-].[Na+]>[CH3:23][O:24][C:25](=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 12575321Methyl 2-[4-(hydroxymethyl)phenyl]acetate

Product 1

HCID 19363032Methyl 2-(4-formylphenyl)acetate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirring solution of Dess-Martin Periodinane (1.5 eq) in dichloromethane (0.3 M) at room temperature under nitrogen was added a solution of 29 in dichloromethane (0.2 M). After 4 hours the reaction was diluted with ether (0.1 M). The reaction mixture was then poured into a solution of sodium thiosulfate (10.5 eq) in saturated sodium bicarbonate (0.5 M) and stirred for 30 minutes. The phases were separated and the organic phase was washed with saturated sodium bicarbonate (1×), H2O (1×) and brine (1×) then dried over sodium sulfate, filtered and concentrated in vacuo to afford the product. (94%) 1H NMR (400 MHz, CDCl3) δ 10.00 (s, 1H), 7.86 (d, 2H), 7.46 (d, 2H), 3.72 (m, 5H).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with saturated sodium bicarbonate (1×), H2O (1×) and brine (1×)
  3. dry with materialthen dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford the product

Sources & evidence

ORD record
ord-bc944cc9411142c0903ff7457914fa84
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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