Hydrochloric Acid → HCID 13817407, compound

HRID 1911978Notes

Reaction equation

HRID 1911978 reaction equation
[CH2:1]([C:8]([CH2:15][S:16][CH3:17])(C(O)=O)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C(CSC)(C(OCC)=O)C(OCC)=O)C1C=CC=CC=1.CO.Cl>O>[CH3:17][S:16][CH2:15][CH:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14086743HCID 14086743, compoundHCID 66610387HCID 66610387, compound

Product 1

HCID 13817407HCID 13817407, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Preparation of 2-benzyl-2-(methylthiomethyl)malonic acid—Powdered potassium hydroxide (4.8 g, 86 mmol, 5.0 equiv) was added to a stirred solution of diethyl 2-benzyl-2-(methylthiomethyl)malonate (5.3 g, 17 mmol, 1.0 equiv) in 3:1 methanol:water (28 mL) at 23° C. The resulting pale yellow suspension was heated to 100° C. and stirred for 4 h. The cooled reaction mixture was acidified to pH≈9 with concentrated hydrochloric acid and washed with diethyl ether (4×50 mL). The aqueous layer was acidified to pH≈1 with concentrated hydrochloric acid and extracted with dichloromethane (4×60 mL). The combined organic layers were dried (Na2SO4), gravity-filtered, and concentrated by rotary evaporation to afford the title compound as a white powder (3.1 g, 72%): 1H NMR (300 MHz, DMSO-d6) δ 7.13-7.34 (m, 5H), 3.15 (s, 2H), 2.73 (s, 2H), 2.08 (s, 3H).

Workup

  1. customat 23° C
  2. customThe cooled reaction mixture
  3. washwashed with diethyl ether (4×50 mL)
  4. extractionextracted with dichloromethane (4×60 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationgravity-filtered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e2c7c77902444d08bc5f102b096a2f82
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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