Ethyl chloroformate → Biphenyl-2,2'-diyl diethyl dicarbonate

HRID 471359

Reaction equation

HRID 471359 reaction equation
[C:1]1([C:8]2[C:9]([OH:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]([OH:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>N1C=CC=CC=1>[C:16](=[O:17])([O:18][CH2:19][CH3:20])[O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:16](=[O:17])[O:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 15731(1,1'-Biphenyl)-2,2'-diol

Product 1

HCID 58288702Biphenyl-2,2'-diyl diethyl dicarbonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a round-bottom flask is charged biphenyl-2,2′-diol (7.45 g, 40 mmol) and pyridine (50 mL). The flask is immersed in an ice-water bath and ethyl chloroformate (9.48 mL, 100 mmol) is added dropwise. After gradually warming to room temperature, the mixture is stirred overnight. The volatiles are removed in vacuo, and the residue is suspended in 100 mL of ethyl acetate. After filtration, the filtrate is concentrated and purified by flash chromatography. The product is obtained as a colorless oil. Yield: 5.0 g; 1H NMR (500 MHz, CDCl3, ppm) δ 7.23-7.44 (m, 8H), 4.13 (q, 4H), 1.19 (t, 6H).

Workup

  1. customThe flask is immersed in an ice-water bath
  2. customThe volatiles are removed in vacuo
  3. filtrationAfter filtration
  4. concentrationthe filtrate is concentrated
  5. custompurified by flash chromatography
  6. customThe product is obtained as a colorless oil

Sources & evidence

ORD record
ord-2b56f5493d7444798e5c727b7761c58b
Source dataset
uspto-grants-2014_01
Patent number
US08633126B2

Linked notes

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