Pyridine → HCID 3468283, compound

HRID 1155141Notes

Reaction equation

HRID 1155141 reaction equation
[OH:1][CH:2]([CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH:7]=1)[CH3:3].N1C=CC=CC=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29](Cl)=[O:30].C(Cl)(=O)C(Cl)=O>C1(C)C=CC=CC=1.O>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29]([O-:1])=[O:30].[OH:1][CH:2]([CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH:7]=1)[CH3:3]

Participants

8

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 109113734-(2-methoxynaphthalen-6-yl)butan-2-ol

Product 2

HCID 3468283HCID 3468283, compoundHCID 109113734-(2-methoxynaphthalen-6-yl)butan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred mixture of 2-hydroxy-4-(6-methoxy-2-naphthyl)butane (1.15 g: 0.005 mole) in toluene (45 ml) containing dry pyridine (3 ml) was added 3,4,5-trimethoxy-benzoyl chloride, prepared from the corresponding acid (1.06 g: 0.005 mole) and oxalyl chloride (1 ml). After standing for 48 hours at room temperature, the resulting mixture was added to water and extracted with ether. The organic extract was washed twice with water, dried (Na2SO4) and concentrated. The crude oil was chromatographed on alumina (100 g) using 10% ethereal hexane as eluant to afford the 3,4,5-trimethoxybenzoate of 2-hydroxy-4-(6-methoxy-2-naphthyl)butane as a pale yellow oil

Workup

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. washwas washed twice with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude oil was chromatographed on alumina (100 g)

Sources & evidence

ORD record
ord-67049b67939e43d397b93dd4e379c516
Source dataset
uspto-grants-1981_11
Patent number
US04299844

Reaction notes

Loading…