Orcinol → HCID 53957774, compound

HRID 442986Notes

Reaction equation

HRID 442986 reaction equation
[C:1]1([OH:9])[CH:8]=[C:6]([CH3:7])[CH:5]=[C:3]([OH:4])[CH:2]=1.C(N(CC)C(C)C)(C)C.[C:19]1([CH2:25][S:26](Cl)(=[O:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C.ClCCl>C(OCC)C>[CH3:7][C:6]1[CH:8]=[C:1]([O:9][S:26]([CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:28])=[O:27])[CH:2]=[C:3]([OH:4])[CH:5]=1

Participants

6

Reactant 4

HCID 10436OrcinolHCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 53957774HCID 53957774, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.0 g (16.1 mmol) of orcinol in diethyl ether (100 mL) containing 10 mL of N,N-diisopropylethylamine was added in a slow steady stream 3.05 g (16 mmol) of α-toluenesulfonyl chloride in a solution of 1:1 diethyl ether/dichloromethane (ca. 30 mL). The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was quenched with 10% hydrochloric acid, extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5 to 90:10)) to give 848 mg of the title compound as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 7.37-7.48 (m, 5H), 6.56-6.57 (m, 1H), 6.51-6.52 (m, 1H), 6.43 (t, 1H, J=2 Hz), 5.21 (s, 1H), 4.50 (s, 2H), 2.26 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with 10% hydrochloric acid
  2. extractionextracted into diethyl ether
  3. dry with materialdried (MgSO4)
  4. custompurified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5 to 90:10))

Sources & evidence

ORD record
ord-8db11f608089462a93a4a2963674dcfe
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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