Dimethyl Sulfoxide → Benzenepentanal

HRID 530501

Reaction equation

HRID 530501 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(CC)CC>C(Cl)Cl>[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 615235-Phenyl-1-pentanolHCID 65578Oxalyl chloride

Product 1

HCID 561886BenzenepentanalYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, at −78° C., to a stirred solution of oxalyl chloride (0.53 mL, 6.17 mmol) in dry CH2Cl2 (12 mL), DMSO (0.40 mL, 5.7 mmol) was added in a fast manner. After 15 min, a solution of 5-phenylpentan-1-ol (0.78 g, 4.75 mmol) in dry CH2Cl2 (6 mL) was added. The reaction mixture was stirred for 2 h at −78° C. before addition of Et3N (1.98 mL, 14.24 mmol). The solution was allowed to warm at rt, and after evaporation of CH2Cl2 the residue was taken up in Et2O and a saturated NH4Cl solution. After separation of phases the organic fraction was dried over Na2SO4, filtered and concentrated to dryness affording the title compound (0.75 g, 97%) as a pure product. 1H NMR (CDCl3): δ 1.67-1.73 (m, 4H), 2.44-2.52 (m, 2H), 2.60-2.71 (m, 2H), 7.16-7.35 (m, 5H), 9.78 (t, J=1.8 Hz, 1H).

Workup

  1. customafter evaporation of CH2Cl2 the residue
  2. customAfter separation of phases the organic fraction
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d6a0389416f749bfae71c7c480d3d8bf
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Linked notes

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