Sulfuric Acid → 3-(2,2-Dimethylpropyl)cyclobutane-1-carbaldehyde

HRID 1912068Notes

Reaction equation

CON(C)[C:4]([CH:6]1[CH2:9][CH:8]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7]1)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH3:12][C:11]([CH3:14])([CH3:13])[CH2:10][CH:8]1[CH2:7][CH:6]([CH:4]=[O:5])[CH2:9]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-methoxy-N-methyl-3-(2,2-dimethylpropyl)cyclobutanecarboxamide (95.2 g) in toluene (330 mL) was added diisobutylaluminum hydride (1.0M in toluene) (486 mL) dropwise at −78° C. After the mixture was stirred at −78° C. for 3 hr, 1.5 M sulfuric acid (648 mL) was added dropwise to the mixture at ice temperature. The mixture was extracted with toluene and the combined organic layer was washed with 1 M sulfuric acid, water and brine, then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate comprising the title compound was used in the next step.

Workup

extractionThe mixture was extracted with toluene
washthe combined organic layer was washed with 1 M sulfuric acid, water and brine
dry with materialdried over sodium sulfate
filtrationThe sodium sulfate was filtered off

Sources & evidence

ORD record: ord-f224179961f54511b5bd4ea08a2394cb
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604069B2

Reaction notes

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