2-Naphthalenesulfonyl chloride → HCID 86743112, compound

HRID 1904428Notes

Reaction equation

HRID 1904428 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28].[OH-].[Na+]>O1CCCC1.C(Cl)Cl>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27]([OH:29])(=[O:8])=[O:28].[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 8400BenzoinHCID 14798Sodium Hydroxide

Product 1

HCID 86743112HCID 86743112, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.1 mole of benzoin and 0.12 mole of β-naphthalenesulfonyl chloride are dissolved at room temperature in 500 ml of tetrahydrofuran. After addition of 0.15 mole of 30% sodium hydroxide solution the mixture is stirred for 8 hours at room temperature. The reaction solution is diluted with 200 ml of methylene chloride and the organic phase is washed once with NaHCO3 solution and once with water. The organic solution is dried over MgSO4, dried and concentrated by evaporation. The residue is crystallised from hexane/ethyl acetate. The resultant sulfonate melts at 107°-109° C.

Workup

  1. washthe organic phase is washed once with NaHCO3 solution and once with water
  2. dry with materialThe organic solution is dried over MgSO4
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe residue is crystallised from hexane/ethyl acetate

Sources & evidence

ORD record
ord-dce09c78cdff4ef0a0c3851e858ab57a
Source dataset
uspto-grants-1989_06
Patent number
US04837350

Reaction notes

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