Hydrochloric Acid → 2-(8-Phenyloctyl)benzaldehyde

HRID 2258278Notes

Reaction equation

HRID 2258278 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:21]=NC(C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(Cl)Cl.[OH2:31]>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:21]=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 19027240HCID 19027240, compound

Product 1

HCID 98176132-(8-Phenyloctyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[(2-(8-phenyloctyl)phenyl)methylene]-1,1-dimethylethanamine (0.51 g, 0.0146 mol) in tetrahydrofuran (5 mL) was added 10% aqueous hydrochloric acid (5 mL) and the mixture stirred for 15 h at room temperature. Methylene chloride (10 mL) and water (10 mL) were added and the layers separated. The aqueous layer was extracted with methylene chloride (1×15 mL) and the combined organics were dried (magnesium sulfate), filtered and concentrated in vacuo to an oil (0.405 g, 97.4% pure by HPLC assay, 92% corrected yield): IR (neat) 2920, 2880, 1695, 1600, 1455 cm-1 ; 1H NMR (CDCl3, 400 MHz) δ 10.25 (s, 1 H), 7.80 (dd, 1 H, J=1.2 and 7.7 Hz), 7.45 (m, 1 H), 7.33-7.13 (m, 7 H), 2.98 (t, 2 H, J=7.7 Hz), 2.58 (t, 2 H, J=7.7 Hz), 1.58 (m, 4 H), 1.30 (m, 8H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with methylene chloride (1×15 mL)
  3. dry with materialthe combined organics were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to an oil (0.405 g, 97.4% pure by HPLC assay, 92% corrected yield)

Sources & evidence

ORD record
ord-f9b2512d9941424ba9f049f3fd166cc5
Source dataset
uspto-grants-1997_08
Patent number
US05659084

Reaction notes

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