O-Cresol → HCID 57871411, compound

HRID 550204Notes

Reaction equation

HRID 550204 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([CH2:18][CH3:19])=[CH:16][CH3:17])[CH:11]=2)[CH:6]=1)=[O:4].[C:20]1([CH3:27])[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][CH:21]=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][CH:9]=[C:10]([C:15]([CH2:18][CH3:19])([C:22]3[CH:23]=[CH:24][C:25]([OH:26])=[C:20]([CH3:27])[CH:21]=3)[CH2:16][CH3:17])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 335O-CresolHCID 8000Boron trifluoride etherateHCID 67158730HCID 67158730, compound

Product 1

HCID 57871411HCID 57871411, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Cool a solution of 6-(1-ethyl-propenyl)naphthalene-2-carboxylic acid methyl ester (0.74 g, 2.75 mmol) and o-cresol (2.0 mL, 19.4 mmol) in CH2CL2 (20 mL) to −78° C.; dropwise add BF3-OEt2 (1.22 mL, 9.6 mmol). Remove the cooling bath and stir the reaction at RT for 16 h. Quench the reaction with ice water; then dilute with EtOAc (200 mL). Wash the resulting mixture twice with brine, dry over Na2SO4, filter, and concentrate the filtrate. Purify the product using medium pressure silica gel chromatography (100% hex to 25:75 EtOAc:hex) to give the title compound as a white solid (0.87 g, 87%). MS (ES) in/e 363 (M+1).

Workup

  1. customRemove the cooling bath
  2. customthe reaction at RT for 16 h
  3. customQuench
  4. customthe reaction with ice water
  5. washWash the resulting mixture twice with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate the filtrate
  9. customPurify the product

Sources & evidence

ORD record
ord-9ceaa72528eb48d88c6202b532df7f29
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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