Dichloromethane → HCID 53730973, compound

HRID 355477Notes

Reaction equation

HRID 355477 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C@H:12]([C@H:14]([C@@H:16]([C@@H:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][CH:23]=2)[OH:19])[OH:17])[OH:15])[OH:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].C(O[C:35](=[O:37])[CH3:36])(=O)C.C(Cl)Cl>N1C=CC=CC=1>[C:1]([O:19][C@@H:18]([C@H:16]([C@@H:14]([C@@H:12]([CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([C:1]([OH:3])=[O:2])=[CH:9][CH:8]=1)[O:13][C:35](=[O:37])[CH3:36])[O:15][C:12](=[O:13])[CH3:11])[O:17][C:7](=[O:10])[CH3:6])[CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=1)(=[O:2])[CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 54335423HCID 54335423, compound

Product 1

HCID 53730973HCID 53730973, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.10 g of 1,6-bis-O-(4-carboxy-phenyl)-D-mannitol were stirred at room temperature for 20 hours in 30 ml of pyridine with 5.1 ml of acetic anhydride. The reaction mixture was worked up extractively with ice-water and methylene chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from methanol and methylene chloride. There was obtained 2,3,4,5-tetra-O-acetyl-1,6-bis-O-(4-carboxy-phenyl)-D-mannitol, MS: m/z 589 ([M-H]-).

Workup

  1. dry with materialThe organic phase was dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was recrystallized from methanol and methylene chloride

Sources & evidence

ORD record
ord-a9fcf58a7bd543ada3093f72bb08030b
Source dataset
uspto-grants-1998_11
Patent number
US05830920

Reaction notes

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