HCID 19591444, compound → Dimethyl 4-hydroxymethylphthalate

HRID 849379Notes

Reaction equation

HRID 849379 reaction equation
[C:1]1([C:14]([O:16][CH3:17])=[O:15])[C:2]([C:10]([O:12][CH3:13])=[O:11])=[CH:3][C:4]([C:7]([O-])=[O:8])=[CH:5][CH:6]=1>O1CCCC1>[OH:8][CH2:7][C:4]1[CH:3]=[C:2]([C:10]([O:12][CH3:13])=[O:11])[C:1](=[CH:6][CH:5]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

3

Reactant 1

HCID 19591444HCID 19591444, compound

Product 1

HCID 22345632Dimethyl 4-hydroxymethylphthalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.43 g of 1,2-dimethyl 1,2,4-benzenetricarboxylate was dissolved in 20 ml of tetrahydrofuran, and 20 ml of a 1M tetrahydrofuran solution of a borane-tetrahydrofuran complex, was added, followed by stirring at room temperature overnight. The reaction solution was extracted by an addition of ethyl ether and water, and the organic layer was post-treated in accordance with a usual method. Then, the product was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→1/1) to obtain 1.31 g of the above identified compound as a colorless oily substance.

Workup

  1. extractionThe reaction solution was extracted by an addition of ethyl ether and water
  2. additionthe organic layer was post-treated in accordance with a usual method
  3. customThen, the product was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→1/1)
  4. customto obtain 1.31 g of the

Sources & evidence

ORD record
ord-60c3c738460641de90353e96f586fb1c
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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