Phenol → HCID 87219631, compound

HRID 1362526Notes

Reaction equation

HRID 1362526 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][CH3:19])[CH2:9][C:10]([C:14]([F:17])([F:16])[F:15])([OH:13])[CH2:11][OH:12])=[C:4]([O:20][CH3:21])[C:3]=1[CH3:22].C1(O)C=CC=CC=1.[NH4+].[Cl-]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][CH3:19])[CH2:9][C:10]([OH:13])([C:14]([F:17])([F:16])[F:15])[CH:11]=[O:12])=[C:4]([O:20][CH3:21])[C:3]=1[CH3:22]

Participants

4

Reactant 3

HCID 996Phenol2×HCID 25517Ammonium ChlorideHCID 66969038HCID 66969038, compound

Product 1

HCID 87219631HCID 87219631, compound

Procedure

1 g (2.93 mmol) of 4-(4-chloro-3-methyl-2-methoxyphenyl)-2-(trifluoromethyl)-hexane-1,2-diol (prepared in analogy to the sequence described in Example 110: acetylation of the corresponding phenol, Fries displacement of the acetyl group, etherification of the phenol, Wittig reaction, ene reaction, reduction of the ester to the alcohol) is reacted conventionally with SO3/pyridine complex. After three-hour stirring at room temperature the reaction mixture is poured onto a mixture of saturated NH4Cl solution and ice. It is extracted three times with methyl tert-butyl ether. The combined organic extracts are washed twice with brine and dried (Na2SO4). Following removal of the solvent on a rotary evaporator, the residue is purified by means of flash chromatography (silica gel, eluent: hexane/ethyl acetate). This gives 290 mg (29.2%) of the desired aldehyde as a mixture of the two diastereomers (in each case as a racemate).

Workup

  1. customis reacted conventionally with SO3/pyridine complex
  2. extractionIt is extracted three times with methyl tert-butyl ether
  3. washThe combined organic extracts are washed twice with brine
  4. dry with materialdried (Na2SO4)
  5. customremoval of the solvent
  6. customon a rotary evaporator
  7. customthe residue is purified by means of flash chromatography (silica gel, eluent: hexane/ethyl acetate)
  8. additionThis gives 290 mg (29.2%) of the desired aldehyde as a mixture of the two diastereomers (in each case as a racemate)

Sources & evidence

ORD record
ord-fca6c4d806514bfa8358e47c0e82850b
Source dataset
uspto-grants-2011_02
Patent number
US07880042B2

Reaction notes

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