4-Hydroxybenzaldehyde → p-(5-n-Octyl-1,3-dioxan-2-yl)phenol

HRID 2050136Notes

Reaction equation

HRID 2050136 reaction equation
[CH2:1]([CH:9]([CH2:12][OH:13])[CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:1]([CH:9]1[CH2:10][O:11][CH:19]([C:18]2[CH:21]=[CH:22][C:15]([OH:14])=[CH:16][CH:17]=2)[O:13][CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 3160622-Octylpropane-1,3-diol

Product 1

HCID 20342141p-(5-n-Octyl-1,3-dioxan-2-yl)phenolYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-n-octylpropane-1,3-diol (5.64 g, 0.03 m), 4-hydroxybenzaldehyde (3.66 g, 0.03 m), benzene (60 ml) and a catalytic amount of 4-toluenesulfonic acid was azeotropically refluxed until no more water was collected (about 16 hours). The solvent was evaporated and the residue was crystallized from 50% aqueous ethanol to yield p-(5-n-octyl-1,3-dioxan-2-yl)phenol (4 g, 48%) mp 96°-97° C.

Workup

  1. customwas collected (about 16 hours)
  2. customThe solvent was evaporated
  3. customthe residue was crystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-528092b16edd4aa092e1cb472ad0013d
Source dataset
uspto-grants-1980_04
Patent number
US04200580

Reaction notes

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