Phenacyl bromide → HCID 21320291, compound

HRID 262219Notes

Reaction equation

HRID 262219 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[C:17]3[CH:18]=[C:19]([CH2:22][C:23](OCC)=[O:24])[CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCC1C=C(O)C=CC=1OC(C)=O.BrCC(C1C=CC=CC=1)=O>CCOCC>[OH:24][CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]2[O:15][CH:14]=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:17]=2[CH:18]=1

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 21226445Aluminium lithium hydrideHCID 46173007HCID 46173007, compoundHCID 53898778HCID 53898778, compound

Product 1

HCID 21320291HCID 21320291, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 200 ml. of diethyl ether and 3.8 g. (0.1 mole) of lithium aluminum hydride under nitrogen is added dropwise a solution of 16 g. (0.057 mole) of ethyl 3-phenylbenzofuran-5-acetate (prepared from ethyl 4-hydroxyphenyl acetate and α-bromoacetophenone by the method described in Belgian Pat. No. 846,502) in 70 ml. of ether at a rate sufficient to maintain reflux for a total of one hour. The reaction is terminated by cautiously adding water (a total of 100 ml.). A 65 ml. portion of 10 percent sulfuric acid is added, the layers are separated and the organic layer is washed twice with water, twice with saturated sodium chloride solution and dried. Evaporation to dryness provides an orange residue of 5-(2-hydroxyethyl)-3-phenylbenzofuran. The structural assignment is confirmed by infrared and nuclear magnetic resonance spectral analysis.

Workup

  1. additionTo a mixture of 200 ml
  2. temperaturereflux for a total of one hour
  3. customThe reaction is terminated by cautiously adding water (a total of 100 ml
  4. additionportion of 10 percent sulfuric acid is added
  5. customthe layers are separated
  6. washthe organic layer is washed twice with water, twice with saturated sodium chloride solution
  7. customdried
  8. customEvaporation to dryness

Sources & evidence

ORD record
ord-97a1d09bd3214254bc4e8563c3338c2d
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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