4-Chlorophenol → Benzene, 1,1'-[oxybis(methyleneoxy)]bis[4-chloro-

HRID 2397308Notes

Reaction equation

HRID 2397308 reaction equation
[C:1]([O:4][CH2:5][O:6][CH2:7][O:8][C:9](=O)[CH3:10])(=O)[CH3:2].[Cl:12][C:13]1[CH:18]=[CH:17]C(O)=C[CH:14]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>ClC1C=CC=CC=1Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:1]([O:4][CH2:5][O:6][CH2:7][O:8][C:9]2[CH:10]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=2)=[CH:2][CH:14]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 77701Methanol, 1,1'-oxybis-, 1,1'-diacetateHCID 9989226Alumina

Product 1

HCID 4215694Benzene, 1,1'-[oxybis(methyleneoxy)]bis[4-chloro-Yield 63.5%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 16.2 g (0.1 mole) of bis(acetoxymethyl) ether and 39 g (0.30 mole) of p-chlorophenol in 80 ml of o-dichlorobenzene were treated with 1.0 g of neutral aluminum oxide (80-240 mesh) and heated to reflux (pot temp. 180°-185° C.). Distillate was removed at about 10 ml/hr over a 4 hour period. The reaction mixture was filtered hot, stripped in vacuo, and triturated with light petroleum ether to furnish 19.0 g (61% yield) of product, mp 53.5°-4° C.

Workup

  1. temperatureheated
  2. temperatureto reflux (pot temp. 180°-185° C.)
  3. customDistillate was removed at about 10 ml/hr over a 4 hour period
  4. filtrationThe reaction mixture was filtered hot
  5. customtriturated with light petroleum ether

Sources & evidence

ORD record
ord-6a280480162b47ac9a8436ac45b2ea9e
Source dataset
uspto-grants-1977_05
Patent number
US04021475

Reaction notes

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