Benzene → HCID 15731889, compound

HRID 2083398Notes

Reaction equation

HRID 2083398 reaction equation
[OH:1][CH2:2][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[CH3:4].[C:9]1([CH3:17])[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:4][C:3]1([CH2:7][OH:8])[CH2:5][O:6][CH:17]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[O:1][CH2:2]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 6502TrimethylolethaneHCID 77254-Methylbenzaldehyde

Product 1

HCID 15731889HCID 15731889, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1,1,1-tris(Hydroxymethyl)ethane (12.0 g), p-tolualdehyde (12.0 g), benzene (100 ml) and toluene-p-sulphonic acid (100 mg) were heated under reflux in a Dean and Stark water trap until no more water separated. The benzene was removed and the crude product was crystallised from light petroleum (b.p. 60°-80°) ethyl acetate as white needles, m.p. 104.5°-105.5°. (cis:trans isomer ratio 82:18). The following compounds were prepared in a similar manner from 1,1,1-tris(hydroxymethyl)ethane and the corresponding aldehyde R1CHO.

Workup

  1. customseparated
  2. customThe benzene was removed
  3. customthe crude product was crystallised from light petroleum (b.p. 60°-80°) ethyl acetate as white needles, m.p. 104.5°-105.5°
  4. customThe following compounds were prepared in a similar manner from 1,1,1-tris(hydroxymethyl)ethane

Sources & evidence

ORD record
ord-4e412758673942f7914b168dd0aea847
Source dataset
uspto-grants-1978_04
Patent number
US04085222

Reaction notes

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