Propylene Oxide → 1-(2'-Hydroxypropyl)-2,2,4-trimethyl decahydroquinoline

HRID 616236Notes

Reaction equation

HRID 616236 reaction equation
[CH2:1]1[O:4][CH:2]1[CH3:3].[CH3:5][C:6]1([CH3:17])[CH2:15][CH:14]([CH3:16])[CH:13]2[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[NH:7]1>C(O)C>[OH:4][CH:2]([CH3:3])[CH2:1][N:7]1[CH:8]2[CH:13]([CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:14]([CH3:16])[CH2:15][C:6]1([CH3:5])[CH3:17]

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 226287862,2,4-Trimethyldecahydroquinoline

Product 1

HCID 205430551-(2'-Hydroxypropyl)-2,2,4-trimethyl decahydroquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2'-hydroxypropyl)-2,2,4-trimethyl decahydroquinoline was prepared by the reaction of 30.2 grams (0.52 mole) of propylene oxide with 90.7 grams (0.5 mole) of 2,2,4-trimethyl decahydroquinoline of about 75% cis structure in the presence of 3 grams of ethanol at 170° C. for 49 hours. The reaction mix was distilled using a 4 inch Vigreaux column to yield 73.1 grams of the desired product, boiling at 93° to 96° C. at 0.26 mm Hg. The NMR and mass spectrometer spectra were consistent with the desired product. The formula C15H29NO has calculated contents of 75.25% carbon, 12.21% hydrogen, and 5.85% nitrogen and the measured contents were 75.42% carbon, 12.77% hydrogen, and 5.62% nitrogen.

Workup

  1. customat 170° C.
  2. customfor 49 hours
  3. additionThe reaction mix
  4. distillationwas distilled

Sources & evidence

ORD record
ord-80d3619c06f4453997ff60bd716e606c
Source dataset
uspto-grants-1978_02
Patent number
US04073770

Reaction notes

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