Sulfuric Acid → Ethyl 3-(4-methylphenyl)-3-oxopropanoate

HRID 2211593Notes

Reaction equation

HRID 2211593 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6](=S)[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[CH3:2].CNC(=N)S.[OH:21]S(O)(=O)=O>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 21962141HCID 21962141, compoundHCID 178485201HCID 178485201, compound

Product 1

HCID 292637Ethyl 3-(4-methylphenyl)-3-oxopropanoate

Procedure

The title compound was prepared from ethyl(4-methylthiobenzoyl)acetate (16.447 g, 69 mmol) (obtained in preparation 3) and methylthiopseudourea.H2SO4 (10.56 g, 38 mmol) according to the procedure described in preparation 4, (1.82 g, 11.5%, mp 266–267° C.). 1H-NMR (DMSO-d6): δ 2.53 (s, 3H), 6.48 (s, 1H), 7.37–7.39 (d, 2H), 7.79–7.81 (d, 2H), 7.92 (bs, 2H). MS m/z: 235 (M+). Preparation 7 Synthesis of 6-(4-methylphenyl)-2H-3,4-dihydro-1,3-oxazin-2,4-dione

Workup

  1. customdescribed in preparation 4, (1.82 g, 11.5%, mp 266–267° C.)

Sources & evidence

ORD record
ord-5b91db2ae14249fab9b4440f53bb55f9
Source dataset
uspto-grants-2006_09
Patent number
US07101873B2

Reaction notes

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