HCID 13502752, compound → 2,2-Dimethyl-3-[(3-phenoxyphenyl)methoxy]propanal

HRID 1194028Notes

Reaction equation

[CH3:1][C:2]([CH3:21])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[CH2:3][OH:4].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[CH3:1][C:2]([CH3:21])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=1)[CH:3]=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2,2-dimethyl-3-(3-phenoxybenzyloxy)-propan-1-ol (15 g) in dry dichloromethane (50 cm3) was added dropwise to a stirred suspension of pyridinium chlorochromate (18.75 g) in dichloromethane (100 cm3) whilst the reaction temperature was maintained within the range 0°-5° C. When the addition was complete, the mixture was allowed to warm to the ambient temperature (ca. 25° C.) over a period of 2 hours. After the reaction mixture had been diluted with diethyl ether, the ethereal layer was decanted and filtered through celite. The solvent was removed by evaporation and the residual oil purified by column chromatography using a silica gel column and eluting with dichloromethane as eluent, to yield 2,2-dimethyl-3-(3-phenoxybenzyloxy)propane-1-al (7.2 g) as an orange oil.

Workup

temperaturewas maintained within the range 0°-5° C
additionWhen the addition
customthe ethereal layer was decanted
filtrationfiltered through celite
customThe solvent was removed by evaporation
customthe residual oil purified by column chromatography
washeluting with dichloromethane as eluent

Sources & evidence

ORD record: ord-c12db069c8804b8090c58e7479c72755
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812483

Reaction notes

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