2,4-Dimethyl-6-tert-butylphenol → 4-(4-Methacryloyloxybutoxy)phenyl 4-allyloxybenzoate

HRID 1637301

Reaction equation

[CH2:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22]Br)=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C(C1C=C(C)C=C(C)C=1O)(C)(C)C.[C:39]([O-:44])(=[O:43])[C:40]([CH3:42])=[CH2:41].[K+]>CN(C)C=O.C1(C)C=CC=CC=1.C(OC)(C)(C)C>[CH2:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:44][C:39](=[O:43])[C:40]([CH3:42])=[CH2:41])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 100 °C

Procedure

118.4 g (0.29 mol) of this ester were dissolved in 50 ml of dimethylformamide at 70° C., 0.3 g of 2-tert-butyl-4,6-dimethylphenol was added as stabilizer, 111.7 g (0.9 mol) of dry potassium methacrylate salt were added, and the mixture was diluted with 70 ml of toluene. The reaction mixture was stirred at 100° C. for 6 h, then cooled and diluted with 800 ml of methyl tert-butyl ether. The precipitate was filtered off with suction, and the washing solution and the filtrate were combined and washed three times with water. They were then concentrated, and the crude product obtained was recrystallized from isopropanol. 4-(4-Methacryloyloxybutoxy)phenyl 4-allyloxybenzoate of m.p. 62-63° C. was obtained in a yield of 83%. Between 41 and 45° C. the ester has a nematic phase which occurs only on supercooling.

Workup

additionwere added
temperaturecooled
filtrationThe precipitate was filtered off with suction
washwashed three times with water
concentrationThey were then concentrated
customthe crude product obtained
customwas recrystallized from isopropanol

Sources & evidence

ORD record: ord-f2119b27a66f42e48695240ef4e4ba8d
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040411

Linked notes

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