6-Phenyl-1-hexanol → HCID 13046675, compound

HRID 1242265Notes

Reaction equation

HRID 1242265 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCCCCC>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 5201106-Phenyl-1-hexanolHCID 178418287HCID 178418287, compound

Product 1

HCID 13046675HCID 13046675, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 6-phenylhexanol (5.00 g, 28.0 mmol, 1 equiv) in CH2Cl2 (10 ml) was added to a solution of pyridinium chlorochromate (9.07 g, 42.1 mmol, 1.5 equiv) in CH2Cl2 (100 ml) at rt, and the mixture was stirred for 3.5 h. The reaction mixture was diluted with hexane and filtered through silica gel (20 g). The silica gel was eluted with a mixture of hexane and EtOAc (1:1). The combined filtrate was concentrated under vacuum to give 6-phenyl-1-hexional as a colorless oil, which was used as such for the next step. 1H NMR (CDCl3) δ 9.75 (t, 1H), 7.28–7.14 (m, 5H), 2.61 (T, 2H), 2.44–2.38 (m, 2H), 1.71–1.58 (m, 5H), 1.42–1.30 (m, 2H).

Workup

  1. filtrationfiltered through silica gel (20 g)
  2. washThe silica gel was eluted with a mixture of hexane and EtOAc (1:1)
  3. concentrationThe combined filtrate was concentrated under vacuum
  4. customto give 6-phenyl-1-hexional as a colorless oil, which

Sources & evidence

ORD record
ord-6e2abcdb37d342e29a4b0b3f5fd77887
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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