Hydrochloric Acid → HCID 12898563, compound

HRID 1680251Notes

Reaction equation

HRID 1680251 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[OH:10].[Cl-].[Al+3].[Cl-].[Cl-].[F:15][C:16]([F:24])([F:23])[C:17]([C:19]([F:22])([F:21])[F:20])=[O:18].Cl>C1(C)C=CC=CC=1>[F:15][C:16]([F:24])([F:23])[C:17]([C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([OH:10])=[C:3]([O:2][CH3:1])[CH:8]=1)([OH:18])[C:19]([F:22])([F:21])[F:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12695HexafluoroacetoneHCID 761732-Methoxy-6-methylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12898563HCID 12898563, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-methoxy-6-methylphenol (27.6 g=0.20 mol) in 300 ml toluene, add aluminum chloride (4.0 g=30 mmol). Bubble in hexafluoroacetone (47 g=0.28 mol) over 7 hours. Heat the reaction mixture in a steel bomb 16 hours at 120° C. Cool, and pour the contents onto 1.0 N HCl. Extract with ether. Wash the ether layer with 1.0 N NaOH. Acidify the basic aqueous layer with concentrated HCl, extract with ether, dry, concentrate and distill to obtain a fraction boiling at 71°-74° C./0.1 mm. Crystallize from cold hexane to obtain, as a solid, m.p. 44°-45° C., 4-(hexafluoro-2-hydroxy-2-propyl)-2-methoxy-6-methylphenol.

Workup

  1. temperatureCool
  2. extractionExtract with ether
  3. washWash the ether layer with 1.0 N NaOH
  4. extractionextract with ether
  5. customdry
  6. concentrationconcentrate
  7. distillationdistill
  8. customto obtain a fraction boiling at 71°-74° C./0.1 mm
  9. customCrystallize from cold hexane

Sources & evidence

ORD record
ord-ece772df03fe47c8892569bc8a77c121
Source dataset
uspto-grants-1981_06
Patent number
US04272550

Reaction notes

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