Hydrochloric Acid → 2-Hydroxynonanedioic acid

HRID 1577691Notes

Reaction equation

HRID 1577691 reaction equation
Br[CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[C:3]([O:5]C)=[O:4].C(=O)([O-])[O-:18].[Na+].[Na+].Cl.[Cl-].[Na+]>O>[OH:18][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 12760707Dimethyl 2-bromononanedioate

Product 1

HCID 127607082-Hydroxynonanedioic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 295 g. of dimethyl 2-bromononanedioate, [Acta. Chim. Acad. Sci. Hung., 46, 85 (1965)], 371 g. of anhydrous sodium carbonate, and 3 liters of water is heated at reflux for 22 hours. The solution which forms is cooled and acidified with 600 ml. of 12N hydrochloric acid. The mixture is saturated with sodium chloride and extracted with ethyl acetate. The extract is washed with brine, dried over magnesium sulfate, and concentrated to give 184 g. of white solid, m.p. 86°-92° C.

Workup

  1. additionA stirred mixture of 295 g
  2. temperatureat reflux for 22 hours
  3. temperatureThe solution which forms is cooled
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give 184 g

Sources & evidence

ORD record
ord-bd1a532e8d404576bf433e036d3f5c8b
Source dataset
uspto-grants-1981_09
Patent number
US04288633

Reaction notes

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