Water → HCID 2769545, compound

HRID 1659559Notes

Reaction equation

HRID 1659559 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15](O)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.B.O.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 1392788(4'-Chloro[1,1'-biphenyl]-4-yl)acetic acid

Product 1

HCID 2769545HCID 2769545, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

Borane-methylsulphide complex (12 ml.) was added to a stirred solution of 2-[4-(4-chlorophenyl)-phenyl]acetic acid (24.7 g.) in tetrahydrofuran (100 ml.), maintained at 4° C. and under an atmosphere of nitrogen. After 1 hour at 4° C., the reaction mixture was allowed to warm up to room temperature and was then stirred for an additional 20 hours. The excess borane was then decomposed by careful addition of water (50 ml.) to the stirred reaction mixture. Ethyl acetate (200 ml.) and a saturated aqueous solution of sodium hydrogen carbonate (200 ml.) was then added to the mixture. After separation, the organic phase was washed with water, dried (MgSO4) and evaporated. The residue was recrystallised from a mixture of hexane and toluene to give 2-[4-(4-chlorophenyl)phenyl]-ethanol (21.5 g.), m.p. 113°-115° C.

Workup

  1. temperatureto warm up to room temperature
  2. customAfter separation
  3. washthe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was recrystallised from a mixture of hexane and toluene

Sources & evidence

ORD record
ord-780213bc7f6e4b39a57f02acb9891e19
Source dataset
uspto-grants-1981_12
Patent number
US04304788

Reaction notes

Loading…