Sodium Bicarbonate → HCID 54409244, compound

HRID 442930Notes

Reaction equation

HRID 442930 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[CH3:11][O:12][C:13]1[C:18]([S:19](Cl)(=[O:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1C.[C:24]([O-])(O)=O.[Na+]>C(OCC)C>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:24])=[CH:17][C:18]=1[S:19]([O:5][C:4]1[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=1)(=[O:20])=[O:21]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 22000404858842-21-4

Product 1

HCID 54409244HCID 54409244, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.00 g (8.05 mmol) of orcinol monohydrate and 1.63 g (7.38 mmol) of 2-methoxy-m-toluenesulfonyl chloride in 20 mL of diethyl ether was added 20 mL of saturated aqueous NaHCO3 and the biphasic mixture stirred vigorously at ambient temperature for 3 days. The layers were separated and the aqueous layer extracted with 2×30 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine, dried (Na2SO4) and concentrated to give 2.2 g of an orange syrup. Crystallization from dichloromethane-hexane (two crops) afforded 1.24 g (54%) of the title compound as a light orange powder: 1H-NMR (300 MHz; CDCl3) δ 7.62 (d, 1 H, J=2.0 Hz), 7.40 (m, 1 H), 6.96 (d, 1 H, J=8.5 Hz), 6.52 (m, 2 H), 6.42 (t, 1 H, J=2.1 Hz), 5.13 (s, 1 H), 3.96 (s, 3 H), 2.29 (s, 3 H) and 2.23 (s, 3 H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with 2×30 mL of ethyl acetate
  3. washThe combined organic layers were washed with 50 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5d35aeb802e47e4aa98f83fd781fe04
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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