Hydrochloric Acid → HCID 131724489, compound

HRID 1883345Notes

Reaction equation

HRID 1883345 reaction equation
[C:1]([OH:11])(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C([O-])([O-])=O.[K+].[K+].CCCCCCCCCCCC.I[C:31]1[CH:32]=[C:33]([CH3:38])[CH:34]=[C:35]([CH3:37])[CH:36]=1.Cl>[Cu]I.CN(C)C(=O)C>[CH3:38][C:33]1[CH:32]=[C:31]([O:10][C:1](=[O:11])[C@H:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[OH:3])[CH:36]=[C:35]([CH3:37])[CH:34]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8182DodecaneHCID 11430Potassium CarbonateHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 439616(S)-mandelic acid

Product 1

HCID 131724489HCID 131724489, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (20 mg, 0.105 mmol, 10 mol %), (S)-mandelic acid (190 mg, 1.25 mmol), K2CO3 (430 mg, 3.11 mmol), evacuated and backfilled with argon. Dodecane (235 μL), 5-iodo-m-xylene (150 μL, 1.04 mmol), and N,N-dimethylacetamide (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 23 h. The resulting pale yellow suspension was poured into 20 mL of 10% aq HCl and extracted with 3×20 mL of dichloromethane. The combined organic phase was dried (Na2SO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane−ethyl acetate−acetic acid 40:20:1; 15 mL fractions). Fractions 7-13 provided 91 mg (34% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 10.65 (br s, 1H), 7.64−7.57 (m, 2H), 7.47−7.36 (m, 3H), 6.67 (s, 1H), 6.61 (s, 2H), 5.65 (s, 1H), 2.28 (s, 6H).

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed
  3. extractionextracted with 3×20 mL of dichloromethane
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×15 cm; hexane−ethyl acetate−acetic acid 40:20:1; 15 mL fractions)

Sources & evidence

ORD record
ord-d638f6ad1d9a41b692fb9359df023783
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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