Ethanol → HCID 23468808, compound

HRID 128302Notes

Reaction equation

HRID 128302 reaction equation
[CH:1]1[C:9]2[C:8]3[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]1[CH:19]([C:20]([O:22]CC)=[O:21])C(O)(C)CC[CH:15]1[C:27]([O:29]CC)=[O:28].[OH-].[Na+].C(O)C>O1CCOCC1.O>[CH:1]1[C:9]2[C:8]3[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]([CH2:19][C:20]([OH:22])=[O:21])[CH2:15][C:27]([OH:29])=[O:28]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 23468786HCID 23468786, compound

Product 1

HCID 23468808HCID 23468808, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 44.2 g (0.1 mol) of diethyl 2-(6,7,8,9-tetrahydro-2-dibenzofuranyl)-4-hydroxy-4-methyl-1,3-cyclohexanedicarboxylate in 250 ml of dioxan is added dropwise to a solution of 120 g (3 mols) of sodium hydroxide in 125 ml of water with 250 ml of ethanol at 90° in the course of 30 minutes. The reaction mixture is heated to 90° for 30 minutes and then concentrated to about 1/3rd of its volume by distilling off the solvents. After diluting the mixture with 750 ml of water, 350 ml of concentrated hydrochloric acid are added, with ice-water cooling. The crude acid which has precipitated is filtered off, washed thoroughly with water and dried. 3-(6,7,8,9-Tetrahydro-2-dibenzofuranyl)-glutaric acid is thus obtained as light yellow-brown crystals of melting point 165°-170°. A sample crystallised from ethanol/water melts at 169°-174°.

Workup

  1. temperatureThe reaction mixture is heated to 90° for 30 minutes
  2. concentrationconcentrated to about 1/3rd of its volume
  3. distillationby distilling off the solvents
  4. additionAfter diluting the mixture with 750 ml of water, 350 ml of concentrated hydrochloric acid
  5. additionare added, with ice-water cooling
  6. customThe crude acid which has precipitated
  7. filtrationis filtered off
  8. washwashed thoroughly with water
  9. customdried

Sources & evidence

ORD record
ord-51e0d210e274466c923c8b76ad20ac6f
Source dataset
uspto-grants-1981_03
Patent number
US04259338

Reaction notes

Loading…