4-Hydroxybenzaldehyde → 4-(2,2,3,3,3-Pentafluoropropoxy)benzaldehyde

HRID 16481

Reaction equation

HRID 16481 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[F:33][C:28]([F:34])([C:29]([F:32])([F:31])[F:30])[CH2:27][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27760172,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

Product 1

HCID 866134424-(2,2,3,3,3-Pentafluoropropoxy)benzaldehydeYield 30.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-hydroxybenzaldehyde (2 g, 16.7 mmol) in DMF (33 mL) was stirred as solid potassium carbonate (4.1 g, 29.7 mmol) was added, and the reaction mixture was then stirred at RT. After 30 min, solid 2,2,3,3,3-pentafluoropropyl 4-methylbenzenesulfonate (5 g, 16.4 mmol) was added into the reaction mixture. The mixture was stirred and heated at 100° C. for 7 h. The reaction mixture was allowed to cool, diluted with ethyl acetate, washed with water (3×) and brine, and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane afforded 4-(2,2,3,3,3-pentafluoropropoxy)benzaldehyde (1.26 g).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred
  3. temperatureheated at 100° C. for 7 h
  4. temperatureto cool
  5. washwashed with water (3×) and brine
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-6643a3580d464da8982c76918c38200a
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Linked notes

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