Hydrochloric Acid → HCID 102004065, compound

HRID 1164256Notes

Reaction equation

HRID 1164256 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[CH:8]([OH:19])[C@H:9]([OH:18])[C@H:10]1[O:15][C:13](=[O:14])[C:12]([OH:16])=[C:11]1[OH:17].[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>O.[N+](C)([O-])=O>[O:19]([CH2:8][C@H:9]([OH:18])[C@H:10]1[O:15][C:13](=[O:14])[C:12]([OH:16])=[C:11]1[OH:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 10340Sodium CarbonateHCID 66700402HCID 66700402, compound

Product 1

HCID 102004065HCID 102004065, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6375NitromethaneSolvent

Procedure

To a stirred solution of 7.44 g (0.06 mol) sodium carbonate in 25 ml of water was added 4.76 g (0.02 mol) of 6-bromo-L-ascorbic acid in small portions, followed by 3.8 g (0.04 mol) of phenol. The solution thickened to a white mobile paste, gradually turning yellow after stirring 6 hours under a nitrogen atmosphere. The reaction mixture was then adjusted to pH 0.5 with 6 N aqueous hydrochloric acid the aqueous solution extracted with ethyl acetate (3×100 ml), the ethyl acetate layer washed with water, brine and dried over anhydrous magnesium sulfate. On removal of solvent in vacuo the residue was triturated with benzene, the resulting crystals collected by filtration and dried under vacuum overnight affording 1.54 g of crude title compound. A sample for analysis was obtained by recrystallization from nitromethane followed by drying under vacuum overnight: mp 160°-161°; VmaxKBr 5.68 (s) 6.00 (s); 1H-nmr (D2O): 7.54-6.75 (m, 5, arom.), 4.93 (broad s, l), 7.20 (m, 3, --CH2 --O and --CH--OH); mass spectrum (70 eV): m/e 252.0563 (parent, C12H12O6, 136 (--O--CH2 --C+H--OH), 116 ##STR4## 107 (--O+ =CH2), 94 (base, --OH); [α]D24 79.3° (C 1.09, CH3OH).

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washthe ethyl acetate layer washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customOn removal of solvent in vacuo the residue
  5. customwas triturated with benzene
  6. filtrationthe resulting crystals collected by filtration
  7. customdried under vacuum overnight
  8. customaffording 1.54 g of crude title compound
  9. customby drying under vacuum overnight

Sources & evidence

ORD record
ord-94c6a8980358447180349f9564179438
Source dataset
uspto-grants-1983_01
Patent number
US04368330

Reaction notes

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