Sodium Hydroxide → 4-Methylbenzaldehyde

HRID 2276353Notes

Reaction equation

HRID 2276353 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([C:6](C2C(NC(=O)C3C=CC=CC=3)=CC3CCCCC=3C=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.C(O)C.O>[C:2]1([CH3:1])[CH:28]=[CH:27][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 69673663HCID 69673663, compound

Product 1

HCID 77254-Methylbenzaldehyde

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 50 mL flask containing a stirred solution of N-[3-(4-methyl-benzoyl)-5,6,7,8-tetrahydro-naphthalen-2-yl]-benzamide (191 mg, 517 μmol) in tetrahydrofuran (5 mL), ethanol (5 mL) and water (1 mL) under nitrogen was added sodium hydroxide (340 mg, 8.5 mmol) and heated at reflux overnight. Heating was discontinued and solvents removed in vacuo. Added water (20 mL) and extracted with ethyl acetate (3×20 mL). Combined organics were dried with magnesium sulphate and evaporated in vacuo to give 3-amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-p-tolyl-methanone as a partially crystalline red oil 146 mg (107% Yield). LCMS (5 min acidic) 2.99 min 100% pure by ELSD and UV ES+ and AP+ 266. HNMR (CDCl3) >90% pure 7.57-7.55 (m, 2H), 7.27-7.24 (m, 2H), 7.16 (s, 1H), 6.46 (s, 1H), 5.63 (br-s, 2H), 2.72-2.69 (m, 2H), 2.59-2.56 (m, 2H), 2.43 (s, 3H), 1.77-1.73 (m, 4H).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureHeating
  4. customsolvents removed in vacuo
  5. extractionAdded water (20 mL) and extracted with ethyl acetate (3×20 mL)
  6. dry with materialCombined organics were dried with magnesium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9184e3ff2a894a21b8efb9ba54830b58
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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