Hydrochloric Acid → 2-Deoxyribose, D-

HRID 1245274Notes

Reaction equation

HRID 1245274 reaction equation
[OH:1][C:2]([CH2:7][C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])(O)C(O)=O.Cl.Cl[O-].[Na+]>C(O)(=O)C>[O:1]=[CH:2][CH2:7][C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665760Sodium Hypochlorite2×HCID 865968002-hydroxy-3-deoxy-D-gluconic acid

Product 1

HCID 54600052-Deoxyribose, D-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The pH of the resulting reaction mixture containing the 2-hydroxy-3-deoxy-D-gluconic acid was adjusted to 5.0 with 35% hydrochloric acid solution. Into the reaction mixture was dripped 377 g of 13% sodium hypochlorite solution to perform decarboxylation over a period of 1 hour with the reaction temperature adjusted to 35° C. The pH of the reaction mixture at this time was adjusted between 5 and 6 with acetic acid. After adding the sodium hypochlorite solution, the reaction was carried out for 1 hour to yield 69 g of 2-deoxy-D-ribose. The yield from sodium D-gluconate was 86.3%.

Workup

  1. customThe pH of the resulting reaction mixture
  2. customof 1 hour
  3. customadjusted to 35° C

Sources & evidence

ORD record
ord-a229a53391354c918657e55aa0052f18
Source dataset
uspto-grants-2006_10
Patent number
US07125704B2

Reaction notes

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