Neopentyl glycol → 4,4'-[2,2-Dimethyl-1,3-propanediylbis(oxycarbonyl)]bis(2,6-dichlorophenol)

HRID 971912

Reaction equation

[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([Cl:20])[C:18]=1[OH:19])[C:12](OC)=[O:13]>C([O-])(=O)C.[Ca+2].C([O-])(=O)C.[Sb]=O>[CH3:1][C:2]([CH3:7])([CH2:5][O:6][C:12]([C:11]1[CH:16]=[C:17]([Cl:20])[C:18]([OH:19])=[C:9]([Cl:8])[CH:10]=1)=[O:13])[CH2:3][O:4][C:12]([C:11]1[CH:16]=[C:17]([Cl:20])[C:18]([OH:19])=[C:9]([Cl:8])[CH:10]=1)=[O:13]

Participants

Conditions

Temperature: 200 °C

Procedure

A mechanically stirred mixture of 0.6 g of calcium acetate, 0.6 g of antimony oxide, 15.7 g (0.15 M) of 2,2-dimethyl-1,3-propanediol, and 132 g (0.6 mole) of methyl 3,5-dichloro-4-hydroxybenzoate was heated under a nitrogen atmosphere at 200° C. for 18 hours. The reaction mixture was washed three times with benzene in a Waring Blendor and extracted for five days with 2 liters of hot benzene. The extract, on cooling, yielded 50.5 g of 4,4'-[2,2-dimethyl-1,3-propanediylbis(oxycarbonyl)]bis(2,6-dichlorophenol) melting at 180°-181° C. The infrared spectrum was consistent with the indicated structure. The compound contained 4.115 meq. of OH/g, indicating a molecular weight of 486 for the bisphenol.

Workup

washThe reaction mixture was washed three times with benzene in a Waring Blendor
extractionextracted for five days with 2 liters of hot benzene
temperatureThe extract, on cooling

Sources & evidence

ORD record: ord-b70fc8f971384e73ba7120c32b99f71a
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04161607

Linked notes

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