3-[(4-Fluoro-3-phenoxyphenyl)methoxy]-2,2-dimethylpropan-1-ol → HCID 13849410, compound

HRID 1200064Notes

Reaction equation

HRID 1200064 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH2:3][OH:4].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:9]=1)[CH:3]=[O:4]

Participants

4

Reactant 2

HCID 138494073-[(4-Fluoro-3-phenoxyphenyl)methoxy]-2,2-dimethylpropan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 13849410HCID 13849410, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propan-1-ol (5.0 g) in dichloromethane (30 cm3) was added dropwise to a stirred suspension of pyridinium chlorochromate (6.77 g) in dichloromethane (20 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 over a period of 2 hours. The solvent was removed and the residual oil (3.0 g) purified by column chromatography using a silica gel column and eluting with a 10:1 (by volume) mixture mixture of petroleum ether (boiling range 40°-60° ) and diethyl ether to yield 2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propan-1-al (1.5 g) as a yellow oil.

Workup

  1. temperaturewas maintained within the range 0°-5° C
  2. additionWhen the addition
  3. customThe solvent was removed
  4. customthe residual oil (3.0 g) purified by column chromatography
  5. washeluting with a 10:1 (by volume) mixture mixture of petroleum ether (boiling range 40°-60° ) and diethyl ether

Sources & evidence

ORD record
ord-e600d0c8559e4b71b0adf469218273fd
Source dataset
uspto-grants-1990_02
Patent number
US04904677

Reaction notes

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