Chloroacetaldehyde → HCID 67155619, compound

HRID 452441Notes

Reaction equation

HRID 452441 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[OH:13].[Cl:14][CH2:15][CH:16]=O.Cl.O>CC(O)=O>[Cl:14][CH2:15][CH:16]1[O:13][C:4]2[CH:5]=[C:6]([C:9]([F:11])([F:12])[F:10])[CH:7]=[CH:8][C:3]=2[CH2:2][O:1]1

Participants

6

Reactant 4

HCID 33Chloroacetaldehyde2×HCID 313Hydrochloric Acid2×HCID 962WaterHCID 552555602-Hydroxy-4-(trifluoromethyl)benzenemethanol

Product 1

HCID 67155619HCID 67155619, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(hydroxymethyl)-5-(trifluoromethyl)phenol (1.0 g, 5.2 mmol) was dissolved in AcOH (4 ml) and cooled on ice-bath. Chloroacetaldehyde (0.93 ml, 7.3 mmol) and concentrated HCl (1.0 ml) were consecutively added drop wise. After 24 h, further addition of chloroacetaldehyde (0.50 ml, 3.9 mmol) and concentrated HCl (1.0 ml) were done and the reaction mixture was allowed to stir another 24 h. Water was added and the aqueous phase was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated under reduced pressure to give an oil. Twice purification by flash column chromatography (isooctane/EtOAc 4:1) gave the pure title compound (0.08 g, 6%). MS m/z (rel. intensity, 70 eV) 252 (M+, 10), 174 (76), 146 (bp), 145 (47), 127 (44).

Workup

  1. temperaturecooled on ice-bath
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give an oil
  6. customTwice purification by flash column chromatography (isooctane/EtOAc 4:1)

Sources & evidence

ORD record
ord-7484a09c1b114b46a044d4b03b6e866c
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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