2-Chloroethanol → Phenol, 4-[(2-chloroethyl)thio]-

HRID 986306Notes

Reaction equation

HRID 986306 reaction equation
[Cl:1][CH2:2]CO.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]#N)=[CH:8][CH:7]=1.C(P(CC)CC)C.C(OCC)C>CC(C)=O.O>[Cl:1][CH2:2][CH2:13][S:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 3283Diethyl EtherHCID 27365TriethylphosphineHCID 2203274-Hydroxyphenyl thiocyanate

Product 1

HCID 13576289Phenol, 4-[(2-chloroethyl)thio]-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-chloro-ethanol (3.9 g, 0.049 mole) was added to a solution of the product of Example 35 (7.4 g, 0.049 mole) in acetone (50 ml). After cooling with an ice bath triethylphosphine (5.6 g, 0.047 mole) was added dropwise over 25 minutes. Ethyl ether (200 ml) and water (75 ml) were added and the layers separated. The organic layer was washed with water (4×50 ml) and saturated sodium chloride (2×25 ml) dried over magnesium sulfate, filtered and concentrated to give a yellow oil. The structure was confirmed by its NMR spectrum.

Workup

  1. additionwas added dropwise over 25 minutes
  2. customthe layers separated
  3. washThe organic layer was washed with water (4×50 ml) and saturated sodium chloride (2×25 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-71344744096c43ee9e45e883f849716f
Source dataset
uspto-grants-1987_12
Patent number
US04711903

Reaction notes

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