4-Hydroxybenzaldehyde → HCID 18459584, compound

HRID 2302132Notes

Reaction equation

HRID 2302132 reaction equation
[C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].C1COCC1.B.[Na].OC1C=CC(C=O)=CC=1>C(OCC)(=O)C.O>[C:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][OH:14])=[CH:11][CH:12]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 8028TetrahydrofuranHCID 118924p-Formylphenyl methacrylateHCID 178418435HCID 178418435, compound

Product 1

HCID 18459584HCID 18459584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the entire amount of the compound obtained in (3-1), 300 ml of THF and 100 ml of water were added and stirred. To this solution, sodium boron hydride was added little by little under ice cooling. Every each addition, disappearance of starting materials was confirmed by TLC. After the starting materials disappeared, water and ethyl acetate were added to the reaction solution and the reaction solution was extracted by liquid separation. The organic phase was dried over magnesium sulfate, concentrated and then subjected to silica gel column chromatography to produce the objective compound. The objective compound was obtained as a slightly brown oily product. Yield: 40.1 g (41.7%) (through two steps from 4-hydroxybenzaldehyde).

Workup

  1. additionwere added
  2. additionEvery each addition, disappearance of starting materials
  3. extractionthe reaction solution was extracted by liquid separation
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto produce the objective compound
  7. customThe objective compound was obtained as a slightly brown oily product

Sources & evidence

ORD record
ord-d5ac8cb13cc14ffeb8aae0c0f8ac937c
Source dataset
uspto-grants-2002_08
Patent number
US06432615B1

Reaction notes

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