1-Naphthalenecarbonyl chloride → HCID 66632460, compound

HRID 1824732Notes

Reaction equation

HRID 1824732 reaction equation
[C:1]1([C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:17]3[C:22]=2[CH:21]=[C:20]([O:23][C:24](=[O:26])[CH3:25])[CH:19]=[CH:18]3)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:37]1(C(Cl)=O)[C:46]2[C:41](=[CH:42][CH:43]=[CH:44]C=2)[CH:40]=[CH:39][CH:38]=1.C(OC1C=CC=C2C=1C=CC(OC(=O)C)=C2)CCCC>C(Cl)Cl>[C:1]1([C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:17]3[C:22]=2[CH:21]=[C:20]([O:23][C:24]([C:25]2[C:46]4[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:42]=[CH:43][CH:44]=2)=[O:26])[CH:19]=[CH:18]3)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 701461-Naphthalenecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 66632655HCID 66632655, compoundHCID 66632899HCID 66632899, compound

Product 1

HCID 66632460HCID 66632460, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Acetic acid 8-(naphthalene-1-carbonyl)-5-pentyloxynaphthalen-2-yl ester: To a stirred suspension of anhydrous aluminium chloride (4.42 g, 33.09 mmol) in anhydrous DCM (290 mL) at 0° C. under nitrogen is added dropwise a solution of naphthoyl chloride (3.7 mL, 24.8 mmol) in anhydrous DCM (35 mL). After 15 min, a solution of acetic acid 5-pentyloxynaphthalen-2-yl ester (4.5 g, 16.54 mmol) in anhydrous DCM (70 mL) is added, and the reaction mixture is allowed to warm to room temperature and stir for 20 h. The mixture is washed with saturated sodium hydrogen carbonate solution, the phases separated and the DCM removed under reduced pressure. The residue is taken up in diethyl ether and washed with water, dried (MgSO4) and the solvent removed under reduced pressure. Purification by chromatography on silica gel (1–3% ethyl acetate in cyclohexane) affords the desired product (4.8 g, 68%) and naphthalene-1-carboxylic acid 8-(naphthalene-1-carbonyl)-5-pentyloxynaphthalen-2-yl ester (2.1 g), arising from naphthoyl replacement of the acetyl group.

Workup

  1. washThe mixture is washed with saturated sodium hydrogen carbonate solution
  2. customthe phases separated
  3. customthe DCM removed under reduced pressure
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customPurification by chromatography on silica gel (1–3% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-28bd12f43642416cb04af5eedfb34302
Source dataset
uspto-grants-2006_05
Patent number
US07045533B2

Reaction notes

Loading…