Hydrochloric Acid → Procromil

HRID 236976Notes

Reaction equation

HRID 236976 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[O:5][C:4]2[C:11]([CH2:19][C:20](=O)[CH3:21])=[C:12]3[C:17](=[CH:18][C:3]1=2)[CH2:16][CH2:15][CH2:14][CH2:13]3.[OH-].[Na+].[BH4-].[Na+].Cl>O>[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[O:5][C:4]2[C:11]([CH2:19][CH2:20][CH3:21])=[C:12]3[C:17](=[CH:18][C:3]1=2)[CH2:16][CH2:15][CH2:14][CH2:13]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20304583HCID 20304583, compound

Product 1

HCID 3085184Procromil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a refluxing solution of 4-oxo-10-(2-oxopropyl)-6,7,8,9-tetrahydro-4H-naphtho[2,3-b]pyran-2-carboxylic acid (3.1 g) in water (100 ml) containing sodium hydroxide (0.12 g) was added portion-wise sodium borohydride (3.04 g). The resulting mixture was heated under reflux for 2 hours. After cooling the solution was acidified with concentrated hydrochloric acid and the precipitate filtered off, washed with water and dried giving the title compound as a white solid, mp 235°.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling the solution
  4. filtrationthe precipitate filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-353a2abd7c154808a349137ec3fedda4
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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