Hydrochloric Acid → 4'-Nonanoyloxybiphenyl-4-carboxylic acid

HRID 442594

Reaction equation

HRID 442594 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:17](Cl)(=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].CN(C1C=CC=CN=1)C.Cl>ClCCl.C(N(CC)CC)C>[C:17]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)(=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 69819Nonanoyl chlorideHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 136684514'-Nonanoyloxybiphenyl-4-carboxylic acidYield 86.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4'-Hydroxybiphenyl-4-carboxylic acid (3.5 g) and triethylamine (2.4 g) were dissolved in dichloromethane (30 ml). Nonanoyl chloride (4.3 g) and dimethylaminopyridine (0.2 g) were added to the solution, and the mixture was stirred at room temperature for about 20 hours. Dilute hydrochloric acid was added thereto, and the organic layer was separated in a separating funnel. The solvent was removed by evaportaion, and the residue was dried after washing with n-hexane to give the titled compound (5 g).

Workup

  1. customthe organic layer was separated in a separating funnel
  2. customThe solvent was removed by evaportaion
  3. customthe residue was dried
  4. washafter washing with n-hexane

Sources & evidence

ORD record
ord-0fbb1e06db2441929e7b81c2113f4d94
Source dataset
uspto-grants-1999_04
Patent number
US05891359

Linked notes

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