Hydrochloric Acid → HCID 22759262, compound

HRID 460837Notes

Reaction equation

HRID 460837 reaction equation
[BH4-].[Na+].[C:3]([CH:6]([CH2:16][CH2:17][CH2:18][CH:19]([OH:29])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:5])[CH3:4].[OH-].[Na+].Cl>CCOCC.O>[OH:5][CH:3]([CH:6]([CH2:16][CH2:17][CH2:18][CH:19]([OH:29])[CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22759241HCID 22759241, compound

Product 1

HCID 22759262HCID 22759262, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium borohydride (1.2 g., 0.03 mole) is added to a solution of 8-acetyl-12-hydroxy-13-(4-fluorophenoxy)-tridecanoic acid (15.4 g., 0.04 mole) and sodium hydroxide (2.0 g., 0.05 mole) in 70 ml. of water. The resulting solution is allowed to stand at room temperature for 19 hours, and is then acidified to Congo Red with concentrated hydrochloric acid. The oily product is taken up in ether, washed with water and dried over sodium sulfate. The ether is evaporated leaving 12.8 g. of the crude title compound as a brown oil.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customThe ether is evaporated
  4. customleaving 12.8 g

Sources & evidence

ORD record
ord-00980e8d16634a08afe712a6dabbf3e4
Source dataset
uspto-grants-1977_12
Patent number
US04061643

Reaction notes

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