Diethyl Ether → HCID 18388545, compound

HRID 2297314Notes

Reaction equation

HRID 2297314 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CCOCC>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]=[O:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 18388551HCID 18388551, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18388545HCID 18388545, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) stirred solution of 3-(4′-heptyloxybiphenyl-4-yl)propan-1-ol (2.26 g, 6.92 mmol) in CH2Cl2 (60 ml) were added molecular sieves 4A powder (5.17 g) and PCC (5.25 g, 24.4 mmol). After being stirred for 2 h at room temperature, Et2O (20 ml) was added to the mixture. The reaction mixture was transferred to a short silica gel column and eluted with CH2Cl2. The eluate was concentrated in vacuo to give 3-(4′-heptyloxybiphenyl-4-yl)propionaldehyde (crude, 2.45 g) which was used for the next step without further purification.

Workup

  1. washeluted with CH2Cl2
  2. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-2bd65bb85c3345fc9c57df745f49ffd1
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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