Triethylamine → HCID 17910428, compound

HRID 2187728Notes

Reaction equation

HRID 2187728 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(OCC)(=O)C>[C:24](=[O:25])([O:26][CH2:27][CH3:28])[O:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[Cl:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 708204-Hydroxy-3,5-dichlorobiphenyl

Product 1

HCID 17910428HCID 17910428, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

40.6 g (0.17 mol) of 3,5-dichloro-4-hydroxybiphenyl (prepared according to J. C. Colbert et al., JACS 56, 202 (1934)) and 17.2 g (0.17 mol) of triethylamine are dissolved in 170 ml of ethyl acetate and admixed dropwise with 18.4 g (0.17 mol) of ethyl chloroformate at 10° C. The reaction solution is stirred overnight and washed with water, and the organic phase is concentrated. For further purification, the crude product (51.2 g) is chromatographed over silica gel using the system chloroform. 48 g (yield 90.8% of theory) of (2,6-dichloro-4-phenyl-phenyl) ethyl carbonate are obtained as an oil, log p (pH 7.5): 4.65.

Workup

  1. washwashed with water
  2. concentrationthe organic phase is concentrated
  3. customFor further purification
  4. customthe crude product (51.2 g) is chromatographed over silica gel using the system chloroform

Sources & evidence

ORD record
ord-470ff53f36254e118014353406276740
Source dataset
uspto-grants-2002_06
Patent number
US06410581B1

Reaction notes

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