Reaction #502073

ord-98e5de63fd55448591c83c53e2f1b3c7

Reaction equation

CC(C)CCCC(C)OCCCCO
4-[(1,5-dimethylhexyl)oxy]butan-1-ol
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
PCC
CC(=O)[O-].[Na+]
sodium acetate
Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
stavox
→
CC(C)CCCC(C)OCCCC=O
desired product
Yield 82.0%
CC(C)CCCC(C)OCCCC=O
4-[(1,5-dimethylhexyl)oxy]butanal
Yield 82.0%

Reactants

CC(C)CCCC(C)OCCCCO
4-[(1,5-dimethylhexyl)oxy]butan-1-ol
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
PCC
CC(=O)[O-].[Na+]
sodium acetate
Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
stavox

Reagents

None

Solvents

ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherA 250 mL 3-necked flask was equipped with a thermocouple pocket, magnetic stirrer and condenser
  2. 2
    workup.STIRRINGThe reaction was stirred for 3 hrs at room temperature

Procedure

A 250 mL 3-necked flask was equipped with a thermocouple pocket, magnetic stirrer and condenser. PCC (13.9 g, 0.64 mols), sodium acetate (1.22 g, 0.015 mol), stavox (0.01 g) and dichloromethane (100 mL) were added to the flask. 4-[(1,5-dimethylhexyl)oxy]butan-1-ol (10.0 g, 0.05 mol) was added over 5 minutes with stirring. The reaction was stirred for 3 hrs at room temperature. After this time the reaction mixture contained ca. 82% of the desired product (RPA GC).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08088725B2uspto-grants-2012_01