Hydrochloric Acid → HCID 86653782, compound

HRID 1528137Notes

Reaction equation

HRID 1528137 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH2:28][CH:29]=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:31]OS([O-])=O.[K+].Cl.C(OC(C)C)(=O)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7915Isopropyl AcetateHCID 23707502Potassium hydroxy sulfiteHCID 86653781HCID 86653781, compound

Product 1

HCID 86653782HCID 86653782, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butanal (450 mg, 1.12 mmol) in DMF (11.5 mL) was added Oxone (350 mg, 1.12 mmol) giving a cloudy white solution. The suspension was stirred vigorously overnight and poured over 10 mL 2.5 M HCl and stirred until the solution clarified. Isopropyl acetate (iPrOAc) (25 mL) was added after the exotherm subsided. The organics were washed 2×10 mL 2.5 M HCl, 1×10 mL saturated aqueous NaCl and dried over Na2SO4. Concentration gave 435 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butanoic acid as a white solid. MS M++H at 419 m/z; 1H NMR (400 MHz, CDCl3) δ=7.50 (m, 4H), 7.43-7.34 (m, 6H), 4.75 (s, 2H), 4.74 (s, 2H), 2.71 (t, 2H), 2.37 (t, 2H), 2.26 (s, 3H), 2.26 (s, 6H), 1.85 (s, 2H) ppm.

Workup

  1. customgiving a cloudy white solution
  2. stirringstirred until the solution
  3. washThe organics were washed 2×10 mL 2.5 M HCl, 1×10 mL saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-1157817b94dd4d6aaaedde19551b5c38
Source dataset
uspto-grants-2015_07
Patent number
US09090576B2

Reaction notes

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