Dimethylformamide → HCID 13520565, compound

HRID 485304Notes

Reaction equation

HRID 485304 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].Cl[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 900121-Octanol, 8-chloro-

Product 1

HCID 13520565HCID 13520565, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-naphthol (28.8 g), 8-chloro-1-octanol (32.8 g), potassium carbonate (40 g) and dimethylformamide (200 ml) was stirred at 60°-65° for 7 days. Water and ether were then added. The a solution was washed with aqueous potassium hydroxide, dried and evaporated. The residue was chromatographed on silica gel, eluting with 95:5 dichloromethane:methanol, and the product so obtained was crystallized from hexane, to give the title compound, mp 67°-9°.

Workup

  1. washThe a solution was washed with aqueous potassium hydroxide
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 95:5 dichloromethane
  6. custommethanol, and the product so obtained
  7. customwas crystallized from hexane

Sources & evidence

ORD record
ord-17cfd6e1e78740cc80e9c475f6c5892e
Source dataset
uspto-grants-1985_08
Patent number
US04536503

Reaction notes

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