Water → HCID 21412653, compound

HRID 2071791Notes

Reaction equation

HRID 2071791 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:21])[C:16](OCC)=[O:17])=[CH:11][C:10]=1[OH:22].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S(=O)(=O)(O)O>CCOCC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:21])[CH2:16][OH:17])=[CH:11][C:10]=1[OH:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 21412650HCID 21412650, compound

Product 1

HCID 21412653HCID 21412653, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of ethyl 2-(2',4'-difluoro-2-hydroxy-4-biphenylyl)propionate (2.0 g.), from the previous Example, in dry ether (40 ml.) was added over 15 minutes in dry ether (40 ml.). After stirring under reflux for 1.5 hours, excess lithium aluminium hydride was decomposed by the cautious addition of water and finally with 2N sulphuric acid (10 ml.). The product was isolated in ether, washed, dried, evaporated and distilled to give a thick translucent oil, setting to a hard glass on cooling. Trituration with boiling light petroleum (b.p. 62°-68° C.) gave a crystalline solid. This was recrystallised from methylene chloride/light petroleum (b.p. 40°-60° C.) to give 2-(2',4'-difluoro-2-hydroxy-4-biphenylyl)propan-1-ol, m.p. 118°-118.5° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. washwashed
  3. customdried
  4. customevaporated
  5. distillationdistilled
  6. customto give a thick translucent oil
  7. temperatureon cooling
  8. customThis was recrystallised from methylene chloride/light petroleum (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-01251b69d97d423e9a44348995db9401
Source dataset
uspto-grants-1977_09
Patent number
US04048332

Reaction notes

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