4-Methoxyphenol → HCID 178444472, compound

HRID 1086774Notes

Reaction equation

HRID 1086774 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14][OH:15])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14][O:15][C:21]2[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 90154-MethoxyphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178444473HCID 178444473, compound

Product 1

HCID 178444472HCID 178444472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.5 g of (E)-3-(trans-4-pentylcyclohexyl)allyl alcohol, 0.3 g of 4-methoxyphenol, 0.4 g of diethyl azodicarboxylate, 0.6 g of triphenylphosphine and 25 ml of absolute tetrahydrofuran was stirred at room temperature overnight and then concentrated. The residue was suspended with 50 ml of hot hexane and filtered. The filtrate was concentrated. Chromatography of the residue on silica gel with toluene/hexane (vol. 1:1) and recrystallization from methanol gave pure 4-methoxyphenyl (E)-3-(trans-4-pentylcyclohexyl)allyl ether with m.p. (C-N) 45° C. and cl.p. (N-I) 46° C.

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customChromatography of the residue on silica gel with toluene/hexane (vol. 1:1) and recrystallization from methanol

Sources & evidence

ORD record
ord-4f508463caf64b2a86d2d77aafb46dad
Source dataset
uspto-grants-1991_07
Patent number
US05032312

Reaction notes

Loading…