4,4'-Dihydroxybiphenyl → HCID 70254186, compound

HRID 1637305Notes

Reaction equation

HRID 1637305 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4](O)=[CH:3][CH:2]=1.BrCCCCCC(Cl)=O.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40].C1C=CC(C2C=CC=CC=2)=CC=1.[C:54]([O-:59])(=[O:58])[C:55]([CH3:57])=[CH2:56].[K+]>C1(C)C=CC=CC=1.CN(C)C=O.O.C(OC)(C)(C)C.C(N(CC)CC)C>[C:54]([O:59][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])(=[O:58])[C:55]([CH3:57])=[CH2:56].[C:54]([O:59][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])(=[O:58])[C:55]([CH3:57])=[CH2:56].[CH:11]1[CH:12]=[CH:13][C:8]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:9][CH:10]=1

Participants

10

Reactant 4

HCID 71124,4'-DihydroxybiphenylHCID 898486-Bromohexanoyl chlorideHCID 23667354Potassium methacrylateHCID 70257042HCID 70257042, compound

Product 1

HCID 70254186HCID 70254186, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
95 °C

Procedure

Following the procedure of Example 6, 18.6 g (0.1 mol) of biphenyl-4,4'-diol (Merck, 64271 Darmstadt, Delaware) were reacted with 42.6 g (0.2 mol) of 6-bromohexanoyl chloride in toluene using triethylamine as acid scavenger. This gave 42 g (77.8%) of 4,4'-biphenyl bis(6-bromohexanoate) of m.p. 96° C. 35 g (0.065 mol) of this compound and 25 g (0.2 mol) of potassium methacrylate were suspended in 30 ml of dimethylformamide, 0.04 g of BHT was added, and the mixture was heated at 95° C. with stirring for 6.5 h. It was then cooled and taken up in water and methyl tert-butyl ether, and the two phases which formed were separated. Washing, drying and concentration of the organic phase gave a crude product which following recrystallization from methanol has a melting range of 50-59° C. and on cooling to 56° C. shows a supercoolable smectic phase.

Workup

  1. addition0.04 g of BHT was added
  2. temperatureIt was then cooled
  3. customwere separated
  4. washWashing
  5. customdrying

Sources & evidence

ORD record
ord-2a62672c48e9440180ec1292e0e06b61
Source dataset
uspto-grants-2000_03
Patent number
US06040411

Reaction notes

Loading…