2,6-Lutidine → 2-Chlorobenzenesulfonic acid 1-hydroxynaphthalen-3-yl ester

HRID 651523Notes

Reaction equation

HRID 651523 reaction equation
[C:1]1([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([OH:11])[CH:2]=1.N1C(C)=CC=CC=1C.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>O1CCCC1>[OH:12][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([O:11][S:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[Cl:21])(=[O:30])=[O:29])[CH:2]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 86011,3-DihydroxynaphthaleneHCID 761872-Chlorobenzenesulfonyl chloride

Product 1

HCID 538375882-Chlorobenzenesulfonic acid 1-hydroxynaphthalen-3-yl esterYield 13.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. to 1.0 g (6.24 mmol) of 1,3-naphthalenediol in tetrahydrofuran (20 mL) containing 1.5 mL of 2,6-lutidine was added 1.35 g (6.40 mmol) of 2-chlorobenzenesulfonyl chloride. The reaction mixture was stirred to ambient temperature overnight, quenched with 3 N hydrochloric acid, extracted into methylene chloride, and dried (MgSO4). Purification by flash chromatography (2% ethyl acetate/methylene chloride) gave 277 mg (13% yield) of the title compound as a colorless solid. 1H-NMR (300 MHz, DMSO-d6) δ 10.75 (s, 1 H), 8.06 (d, 1 H, J=1.7 Hz), 7.78-7.95 (m, 4 H), 7.43-7.57 (m, 3 H), 7.11 (d, 1 H, J=2 Hz), and 6.63 (d, 1 H, J=2 Hz).

Workup

  1. customquenched with 3 N hydrochloric acid
  2. extractionextracted into methylene chloride
  3. dry with materialdried (MgSO4)
  4. customPurification by flash chromatography (2% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-4fed3cb83cd9473f824f359e8ad8d040
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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