1,1'-Carbonyldiimidazole → [4-(2-Chloroethyl)phenyl]methanol

HRID 564038Notes

Reaction equation

HRID 564038 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+]>C1COCC1>[Cl:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 887124-(2-Chloroethyl)benzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 53929068[4-(2-Chloroethyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 100 g (525 mmol) 4-(2-chloro-ethyl)-benzoic acid in 1.0 L of THF is added 170 g (1050 mmol) CDI in small portions. The mixture is stirred at 60° C. until the gas evolution ceased. After cooling to RT, the mixture is slowly added into a solution of 39.7 g (1050 mmol) sodium borohydride in ice water and is stirred for 3 h at RT. The solution is acidified with diluted HCL and extracted twice with EtOAc. The organic phase is separated and dried over MgSO4. After evaporation of the solvent, the residue is dissolved in water/EtOAc. The aqueous phase is separated, washed once with EtOAc and the combined organic phase is dried over MgSO4. After evaporation of the solvent the residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent.

Workup

  1. temperatureAfter cooling to RT
  2. stirringis stirred for 3 h at RT
  3. extractionextracted twice with EtOAc
  4. customThe organic phase is separated
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvent
  7. dissolutionthe residue is dissolved in water/EtOAc
  8. customThe aqueous phase is separated
  9. washwashed once with EtOAc
  10. dry with materialthe combined organic phase is dried over MgSO4
  11. customAfter evaporation of the solvent the residue
  12. customis purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent

Sources & evidence

ORD record
ord-de22c1ac47fa4c18b66c7c21877b478b
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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