Nitrosobis(2-hydroxypropyl)amine → 2,6-Naphthalenedimethanol, alpha,alpha,alpha',alpha'-tetramethyl-

HRID 1614411Notes

Reaction equation

HRID 1614411 reaction equation
CC(O)CN(N=O)CC(O)C.[O:12]([C:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:27]([O:30]O)([CH3:29])[CH3:28])[CH:23]=2)[CH:18]=1)([CH3:16])[CH3:15])[OH:13]>>[OH:30][C:27]([C:22]1[CH:21]=[CH:20][C:19]2[C:24](=[CH:25][CH:26]=[C:17]([C:14]([O:12][OH:13])([CH3:16])[CH3:15])[CH:18]=2)[CH:23]=1)([CH3:28])[CH3:29].[OH:12][C:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:27]([OH:30])([CH3:29])[CH3:28])[CH:23]=2)[CH:18]=1)([CH3:16])[CH3:15].[O:12]([C:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH:27]([CH3:29])[CH3:28])[CH:23]=2)[CH:18]=1)([CH3:16])[CH3:15])[OH:13].[OH:12][C:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH:27]([CH3:29])[CH3:28])[CH:23]=2)[CH:18]=1)([CH3:16])[CH3:15]

Participants

6

Reactant 2

HCID 40828Nitrosobis(2-hydroxypropyl)amineHCID 13781869HCID 13781869, compound

Product 4

HCID 1855582,6-Naphthalenedimethanol, alpha,alpha,alpha',alpha'-tetramethyl-HCID 1862962-(6-Propan-2-ylnaphthalen-2-yl)propan-2-olHCID 9816285Hydroperoxide, 1-methyl-1-[6-(1-methylethyl)-2-naphthalenyl]ethylHCID 13781870HCID 13781870, compound

Procedure

The DIPN conversion was 92.8 mol %, and the yield of 2,6-bis(2-hydroperoxy-2-propyl)naphthalene was 33.4 mol %. In addition, 2-(2-hydroxy-2-propyl)-6-(2-hydroperoxy-2-propyl)-naphthalene, 2,6-bis(2-hydroxy-2-propyl)naphthalene, 2-(2-hydroperoxy-2-propyl)-6-isopropylnaphthalene, and 2-(2-hydroxy-2-propyl)-6-isopropylnaphthalene were produced in yields of 19.1 mol %, 3.3 mol %, 25.2 mol %, and 8.9 mol %, respectively. The conversion of the isopropyl groups was 75.8 mol %.

Sources & evidence

ORD record
ord-b96a6462bde6496982993bcaf0f66a4c
Source dataset
uspto-grants-1993_03
Patent number
US05196598

Reaction notes

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