Sodium Hydroxide → HCID 21397410, compound

HRID 1730223Notes

Reaction equation

HRID 1730223 reaction equation
[C:1]([C:4]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH2:16][CH2:17][CH2:18][CH:19]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:4]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH2:16][CH2:17][CH2:18][CH:19]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21397385HCID 21397385, compound

Product 1

HCID 21397410HCID 21397410, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 8-acetyl-8-phenyl-12-benzyloxyheptadecanoate (14 g., crude), sodium hydroxide (2.0 g., 0.05 mole) and methanol (150 ml.) is stirred for 48 hours. The methanol is removed in vacuo; and the residual oil is poured into H2O (100 ml.), acidified with 6 N HCl (100 ml.), extracted with ether, and the combined ether extracts dried over anhydrous Na2SO4. The ether is removed in vacuo, and the residual oil is chromatographed through a silica gel column (95% CHCH3 -5% MeOH) to obtain 8-acetyl-8-phenyl-12-benzyloxyheptadecanoic acid (1.43 g., slightly impure).

Workup

  1. customThe methanol is removed in vacuo
  2. additionand the residual oil is poured into H2O (100 ml.)
  3. extractionextracted with ether
  4. dry with materialthe combined ether extracts dried over anhydrous Na2SO4
  5. customThe ether is removed in vacuo
  6. customthe residual oil is chromatographed through a silica gel column (95% CHCH3 -5% MeOH)

Sources & evidence

ORD record
ord-fd640f23df184399876a7e6be45c58b2
Source dataset
uspto-grants-1976_11
Patent number
US03991087

Reaction notes

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