4,4'-Dihydroxybiphenyl → HCID 19809919, compound

HRID 373465Notes

Reaction equation

HRID 373465 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.[C:30]([C@:32]([CH3:40])([CH2:36][CH2:37][CH2:38][CH3:39])[C:33](O)=[O:34])#[N:31]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:30]([C:32]([CH3:40])([CH2:36][CH2:37][CH2:38][CH3:39])[C:33]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:21][CH:22]=1)=[O:34])#[N:31]

Participants

6

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 10868DicyclohexylcarbodiimideHCID 14495734HCID 14495734, compound

Product 1

HCID 19809919HCID 19809919, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

a solution of 22.7 g of DCCI in 20 ml of CH2Cl2 is added at 0° to a mixture of 18.6 g of 4,4'-dihydroxy-1,1'-biphenyl, 15.5 g of (S)-2-cyano-2-methylhexanoic acid, 1.2 g of 4-dimethylaminopyridine and 100 ml of CH2Cl2, and the mixture is stirred at room temperature for 2 hours. The precipitate is filtered off with suction, the filtrate is concentrated and chromatography over silica gel gives 4'-(2-cyano-2-methylhexanoyloxy)-4-hydroxy-1,1'-biphenyl (optically active).

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-2d78037eddab4e889cdeead38b1e6747
Source dataset
uspto-grants-1992_11
Patent number
US05164111

Reaction notes

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