Tetrahydrofuran → 2-(4-Chlorophenyl)-1-propanol

HRID 1704127Notes

Reaction equation

HRID 1704127 reaction equation
B#B.[Cl:3][C:4]1[CH:15]=[CH:14][C:7](OC(C)C(O)=O)=[CH:6][CH:5]=1.[O:16]1C[CH2:19][CH2:18][CH2:17]1>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:18]([CH3:19])[CH2:17][OH:16])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 187032-(4-Chlorophenoxy)propionic acidHCID 6328200Diboron

Product 1

HCID 5870302-(4-Chlorophenyl)-1-propanol

Procedure

To 833 ml. of a chilled solution (0° C.) of 1M diborane in tetrahydrofuran is added dropwise a solution of 96 g. of 2-(p-chlorophenoxy)propionic acid in 500 ml. of tetrahydrofuran. The reaction mixture is stirred for 2 days at room temperature and then poured onto 2 kg. of ice/water. The resulting mixture is extracted with diethyl ether and the extract is washed with water and dried over MgSO4. The solvent is removed under vacuum and the residual liquid is distilled to give 83 g. (b.p. 116°-120° C./0.1 mm.) of product.

Workup

  1. additionpoured onto 2 kg
  2. extractionThe resulting mixture is extracted with diethyl ether
  3. washthe extract is washed with water
  4. dry with materialdried over MgSO4
  5. customThe solvent is removed under vacuum
  6. distillationthe residual liquid is distilled
  7. customto give 83 g

Sources & evidence

ORD record
ord-005bbc6adeea4ca3bb601f8ef036d540
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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