1-Octanol → HCID 19025175, compound

HRID 1033145Notes

Reaction equation

HRID 1033145 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19](Cl)=[O:20])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.CCCCCC.C([O:55]C(=O)C)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:55])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 9571-OctanolHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 144384196-(Benzyloxy)naphthalene-2-carbonyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 19025175HCID 19025175, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-benzyloxynaphthalene-6-carboxylic acid chloride (6.4 g) was dissolved in 50 ml of methylene chloride and added in small portions to a solution of 1-octanol (2.6 g), dimethylaminopyridine (0.7 g) and triethylamine (2.1 g) in 30 ml of methylene chloride under ice-cooling. After the reaction mixture was stirred for about 20 hours, it was poured into ice-water and extracted with methylene chloride. The solvent was removed by evaporation to give a crude product, which was then subjected to silica gel column chromatography (eluent: hexane/ethylacetate=10/0.5) to give 2.6 g of 2-benzyloxy-6-octyloxycarbonylnaphthalene.

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. customThe solvent was removed by evaporation
  4. customto give a crude product, which

Sources & evidence

ORD record
ord-e5ae2b67473f4ccaa9c146f07b0af2de
Source dataset
uspto-grants-1994_05
Patent number
US05310500

Reaction notes

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