Hydrochloric Acid → 2-(Phenylthiomethyl)-5-ethylbenzoic acid

HRID 2177687Notes

Reaction equation

HRID 2177687 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([C:10]1[CH:18]=[C:17]2[C:13]([CH2:14][O:15][C:16]2=[O:19])=[CH:12][CH:11]=1)[CH3:9].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O>[C:1]1([S:7][CH2:14][C:13]2[CH:12]=[CH:11][C:10]([CH2:8][CH3:9])=[CH:18][C:17]=2[C:16]([OH:19])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 593824426-ethyl-3H-isobenzofuran-1-one2×

Product 1

HCID 671074512-(Phenylthiomethyl)-5-ethylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Thiophenol (0.128 ml) was added to a mixture of 6-ethyl-3H-isobenzofuran-1-one (Intermediate 18, 0.202 g) and potassium carbonate (0.344 g) in dry DMF (1.3 ml). The resultant mixture was stirred and heated at 110° C. for 2 hours. After cooling, the mixture was diluted with water and acidified by addition of hydrochloric acid (1M). The resultant solid was collected by filtration, washed with water and dried under vacuum to give 2-(phenylthiomethyl)-5-ethylbenzoic acid (0.288 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2a7e907d227b4b0eb5396d7ddcbc8d49
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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