O-Cresol → HCID 57871398, compound

HRID 550217Notes

Reaction equation

HRID 550217 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([CH2:19][CH3:20])(O)[CH2:16][CH3:17])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[C:21]1([CH3:28])[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][CH:22]=1.B(F)(F)F.O(CC)CC>CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([CH2:19][CH3:20])([C:23]3[CH:24]=[CH:25][C:26]([OH:27])=[C:21]([CH3:28])[CH:22]=3)[CH2:16][CH3:17])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 335O-CresolHCID 8000Boron trifluoride etherateHCID 57871419HCID 57871419, compound

Product 1

HCID 57871398HCID 57871398, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Cool a CH2CL2 (20 mL) solution of 7-(1-ethyl-1-hydroxypropyl)naphthalene-2-carboxylic acid methyl ester (0.73 g, 2.68 mmol) and o-cresol (1.54 mL, 15.0 mmol) to −78° C.; then dropwise add BF3-OEt2 (0.76 mL, 6.0 mmol). Allow the reaction mixture to warm to RT and stir for 1 h. Quench the reaction with ice water. Dilute the resulting mixture with EtOAc (200 mL). Wash the mixture with brine, dry the organic layer over Na2SO4, filter and concentrate the filtrate. Purify by silica gel radial chromatography (5:95 to 35:65 EtOAc:hex) to give the title compound as a yellow oil (0.93 g, 86%). MS (ES) m/e 363 (M+1).

Workup

  1. customQuench
  2. customthe reaction with ice water
  3. washWash the mixture with brine
  4. dry with materialdry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate the filtrate
  7. customPurify by silica gel radial chromatography (5:95 to 35:65 EtOAc:hex)

Sources & evidence

ORD record
ord-27fa6b0de70f4904b7a73661ccb7a076
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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