Phenyl glycidyl ether → 1-(2'-Hydroxy-3'-phenoxy propyl)-2,2,4-trimethyl decahydroquinoline

HRID 616238Notes

Reaction equation

HRID 616238 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:11][CH:10]([CH3:12])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.[O:14]1[CH:16]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15]1>C(O)C>[OH:14][CH:16]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:15][N:3]1[CH:4]2[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:10]([CH3:12])[CH2:11][C:2]1([CH3:13])[CH3:1]

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 226287862,2,4-Trimethyldecahydroquinoline

Product 1

HCID 205430961-(2'-Hydroxy-3'-phenoxy propyl)-2,2,4-trimethyl decahydroquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2'-hydroxy-3'-phenoxy propyl)-2,2,4-trimethyl decahydroquinoline was prepared using a process similar to those described above. 27.2 grams (0.15 mole) of about 75% cis structure 2,2,4-trimethyl decahydroquinoline was reacted with 22.5 grams (0.15 mole) of 1,2-epoxy-3-phenoxy propane in the presence of 0.5 gram of ethanol at 160° C. for 19 hours. The reaction mixture was distilled to yield 21.2 grams of a liquid product boiling at 168° C. at 0.2 mm Hg. The infrared and mass spectrometer spectra are consistent with the desired product. Calculated values for C21H34NO2 were 75.85% carbon, 10.31% hydrogen, and 4.21% nitrogen, while measured values were 74.67% carbon, 10.18% hydrogen, and 4.26% nitrogen.

Workup

  1. distillationThe reaction mixture was distilled

Sources & evidence

ORD record
ord-1412825b7d4b4b078386da431a3bcfe7
Source dataset
uspto-grants-1978_02
Patent number
US04073770

Reaction notes

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