Sodium Hydroxide → HCID 21397410, compound

HRID 1439486Notes

Reaction equation

HRID 1439486 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-7f6b93c755074f22a25bc718c4c81a11
Source dataset
uspto-grants-1977_11
Patent number
US04059602

Reaction notes

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