Benzene → HCID 86734263, compound

HRID 1973452Notes

Reaction equation

HRID 1973452 reaction equation
[OH:1][C@@H:2]([CH3:41])[CH2:3][CH2:4][CH:5]1[O:40][CH2:39][CH2:38][O:37][CH:6]1[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[C:17]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:13]=1[C:14]([OH:16])=[O:15].[CH:42]1C=CC=CC=1.[N+](=C)=[N-].CN(N=O)C(N)=O>C(O)(=O)C.C(OCC)C>[OH:1][C@@H:2]([CH3:41])[CH2:3][CH2:4][CH:5]1[O:40][CH2:39][CH2:38][O:37][CH:6]1[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:18]=[C:17]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:13]=1[C:14]([O:16][CH3:42])=[O:15]

Participants

7

Reactant 4

HCID 241BenzeneHCID 9550Diazomethane4×HCID 12699N-Methyl-N-nitrosoureaHCID 86734264HCID 86734264, compound

Product 1

HCID 86734263HCID 86734263, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 48 g. of 2-(10(S)-hydroxy-6-ethylenedioxy-trans-undecenyl)-4,6-dibenzyloxybenzoic acid in 300 ml. of benzene is added a stoichiometric excess of diazomethane in 250 ml. of diethyl ether. The diazomethane is freshly prepared from N-methylnitrosourea. The solution becomes light yellow and is stirred for 15 minutes after the addition of the diazomethane. Acetic acid is then added to the mixture to decompose the excess diazomethane, and the solvents are removed to provide 48.8 g. of light yellow oil. The oil is purified by chromatography on 1250 g. of SilicAR, CC-7, an absorbent silica gel obtainable from Mallinckrodt Chemical Works, using a chloroform solvent. About 41 g. of a colorless oil of methyl 2-(10(S)-hydroxy-6-ethylenedioxy-trans-undecenyl)-4,6-dibenzyloxybenzoate are obtained. This oil analyzes as containing 72.92 wt. % carbon and 7.24 wt. % hydrogen, as compared to theoretical values of 73.17 wt. % carbon and 7.32 wt. % hydrogen.

Workup

  1. additionTo a suspension of 48 g
  2. customthe solvents are removed
  3. customto provide 48.8 g
  4. customThe oil is purified by chromatography on 1250 g

Sources & evidence

ORD record
ord-464ca215b692461396bfe374a813e888
Source dataset
uspto-grants-1976_12
Patent number
US03997568

Reaction notes

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