Potassium Carbonate → HCID 86639022, compound

HRID 907776Notes

Reaction equation

HRID 907776 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:23]=[CH:22][C:8]([CH2:9][N:10]([CH3:21])[C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)C.C(=O)([O-])[O-].[K+].[K+]>Cl>[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH3:21])[C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:22][CH:23]=1)=[O:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67258220HCID 67258220, compound

Product 1

HCID 86639022HCID 86639022, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The mixture of benzyl 4-(diethoxymethyl)benzyl(methyl)carbamate (1.0 g, 2.8 mmol) in 3N hydrochloric acid (50 ml) was stirring at room temperature for 1 h. Then the mixture was neutralized with Potassium carbonate. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and concentrated to give benzyl 4-formylbenzyl(methyl)carbamate (730 mg, 92%). 1H-NMR (400 MHz, CDCl3) δ: 2.94 (d, 3H), 4.572 (d, 2H), 5.18 (d, 2H), 7.32-7.39 (m, 7H), 7.84 (m, 2H), 10.00 (s, 1H); LC-MS (ESI) m/z: 284 (M+1)+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  2. washthe organic phase was washed with water and saturated sodium bicarbonate
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ac9fa7030be04826b66fb3dd68c0cd35
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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