Hydrochloric Acid → HCID 15124017, compound

HRID 1084867Notes

Reaction equation

HRID 1084867 reaction equation
[O-]CC.[Na+].[Na].[C:6]([C:9]1[C:21]([OH:22])=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=[CH:18][C:10]=1[O:11][CH2:12]C(OCC)=O)(=O)[CH3:7].Cl>C(O)C>[CH3:7][C:6]1[C:9]2[C:21]([OH:22])=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[CH:19]=[CH:18][C:10]=2[O:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 15124016HCID 15124016, compound

Product 1

HCID 15124017HCID 15124017, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide freshly prepared from sodium metal (0.104 g, 4.50 mmol) in ethanol (25 mL) was added ethyl 2-(2-acetyl-3-hydroxy-4-tert-butylphenoxy)acetate 11b (1.26 g, 4.28 mmol) and the mixture heated to reflux for 10 minutes. The reaction mixture was cooled and acidified by pouring into 2N HCl (75 mL). The resulting solution was extracted with ethyl acetate (2×35 mL) and the combined extracts dried (Na2SO4), and concentrated. Flash chromatography afforded, in order of elution 3-methyl-4-hydroxy-5-tert-butylbenzofuran, compound 12b. mp 79°-81° C.; 1H NMR d 1.49 (9H, s), 2.48 (3H, s), 5.27 (1H, s), 7.00 (1H, d, J=8 Hz), 7.24 (1H, d, J=8 Hz), 7.26 (1H, s) and ethyl 3-methyl-4-hydroxy-5-tert-butylbenzofuran-2-carboxylate, compound 12 a, mp. 109-112 (from hexane); 1H NMR d 1.42 (3H, J=6 Hz), 1.46 (9H, s), 2.83 (3H, s), 4.43 (2H, q, J=6 Hz), 5.45 (1H, br s), 7.04 (1H, d, J=8 Hz), 7.37 (1H, d, J=8 Hz).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 10 minutes
  3. temperatureThe reaction mixture was cooled
  4. extractionThe resulting solution was extracted with ethyl acetate (2×35 mL)
  5. dry with materialthe combined extracts dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a80114b076b74e7ca653d452782f50d0
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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