Toluene → 2-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

HRID 1938838Notes

Reaction equation

HRID 1938838 reaction equation
[C:1]1(C)C=CC=C[CH:2]=1.C(=O)(O)[O-].[Na+].[OH-].[K+].[C:15]([C:18]1[S:19][CH2:20][CH2:21][O:22][C:23]=1[CH3:24])([OH:17])=[O:16]>C1C=CC=CC=1>[CH3:24][C:23]1[O:22][CH2:21][CH2:20][S:19][C:18]=1[C:15]([O:17][CH2:1][CH3:2])=[O:16].[CH3:24][C:23]1[O:22][CH2:21][CH2:20][S:19][C:18]=1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

Product 2

HCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acidHCID 540271HCID 540271, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylate was prepared by the method of U.S. Pat. No. 3,249,499 (col. 5, lines 36-55), with the following modifications: toluene was used as the solvent instead of benzene, sodium bicarbonate was used as the base instead of potassium hydroxide, and the azeotropic removal of water was carried out under reduced pressure at about 65° C. 5,6-Dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid was prepared by hydrolysis of the ester as described in the same patent (col. 5, lines 56-68, where the acid is named 2,3-dihydro-5-carboxy-6-methyl-1,4-oxathiin).

Workup

  1. customthe azeotropic removal of water
  2. customwas carried out under reduced pressure at about 65° C

Sources & evidence

ORD record
ord-3e724cfe1ece432bba5420a23cf78376
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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