Acetaldehyde → HCID 21547111, compound

HRID 1605647Notes

Reaction equation

HRID 1605647 reaction equation
[CH:1](=O)[CH3:2].BrCC[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19].[Mg].Cl.CC[O:24][CH2:25][CH3:26]>>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:8]1[CH:7]=[CH:12][C:11]([CH2:1][CH2:2][CH:25]([OH:24])[CH3:26])=[CH:10][CH:9]=1

Participants

6

Reactant 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 5462224MagnesiumHCID 21547143HCID 21547143, compound

Product 1

HCID 21547111HCID 21547111, compound

Procedure

A solution of 5.82 gm (0.132 mol) of acetaldehyde in 10 ml of dry ether was added dropwise to a stirred Grignard reagent prepared under exclusion of air from 47.0 gm (0.168 mol) of 1-bromo-2-(2'-fluoro-biphenylyl)-ethane and 4.0 gm (0.165 mol) of magnesium in 60 ml of anhydrous ether. All of these operations were carried out in an atmosphere of very pure nitrogen. The resulting mixture was heated for 2 hours on a water bath, while stirring, then cooled and hydryolized by addition of 50 gm of crushed ice, and subsequently half-concentrated hydrochloric acid was added until the precipitate which had formed just went into solution again. The ethereal phase was separated, the aqueous phase was extracted twice with ether, and the ethereal extracts were combined with the ethereal phase, washed with water, with an aqueous saturated sodium bicarbonate solution and again with water, dried over sodium sulfate and evaporated. The residue was recrystallized twice from petroleum ether in the presence of activated charcoal, yielding 9.0 gm (28% of theory) of the colorless crystalline compound of the formula ##SPC23##

Workup

  1. temperatureThe resulting mixture was heated for 2 hours on a water bath
  2. additionwas added until the precipitate which
  3. customhad formed just
  4. customThe ethereal phase was separated
  5. extractionthe aqueous phase was extracted twice with ether
  6. washwashed with water, with an aqueous saturated sodium bicarbonate solution and again with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was recrystallized twice from petroleum ether in the presence of activated charcoal
  10. customyielding 9.0 gm (28% of theory) of the colorless crystalline compound of the formula

Sources & evidence

ORD record
ord-0060f8b51c7f4915ab1b77358f03b277
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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