Hydrochloric Acid → 1,5-Anhydro-D-mannitol

HRID 1987677Notes

Reaction equation

HRID 1987677 reaction equation
CC1(C)[O:7][C@H:6]2[C@H:8]([OH:13])[C@H:9]([OH:12])[CH2:10][O:11][C@@H:5]2[CH2:4][O:3]1.Cl>CO>[OH:3][CH2:4][C@@H:5]1[C@@H:6]([OH:7])[C@H:8]([OH:13])[C@H:9]([OH:12])[CH2:10][O:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57723950HCID 57723950, compound

Product 1

HCID 4451841,5-Anhydro-D-mannitol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (−)-(4aR,7R,8R,8aS)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (42 mg, 0.21 mmol) in MeOH (2 mL) was added a solution of methanolic HCl (0.6 mL, prepared from 0.5 mL conc. HCl in 30 mL of MeOH). The solution was stirred for 1H at ambient temperature and concentrated in vacuo.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8c4d81bb70348fb8e4aa268704a6bf1
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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