Acetic Acid → HCID 19818307, compound

HRID 1086790Notes

Reaction equation

HRID 1086790 reaction equation
[CH2:1]([C:10]1[C:11](O)=[C:12]([C:17]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21](CCCCCCCCC)[C:20]=2[OH:35])=[O:18])C=C(C)C=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]CCC.B.[Na].C(O)(=O)C>C(O)C.O.[OH-].[Na+]>[OH:18][CH:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[OH:35])[CH2:12][CH2:11][CH2:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 67924456HCID 67924456, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 19818307HCID 19818307, compoundYield 25.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

52.5 g of n-nonyl-2-hydroxy-5-methylphenylketone were dissolved in 100 ml of ethanol. A solution of 9.1 g of sodium boron hydride dissolved in 50 ml of water containing 1.1 g of sodium hydroxide was added dropwise thereto. The mixture was stirred at 40° C. for 2 hours. 100 ml of water was added thereto. Further, 20 ml of acetic acid was slowly added dropwise thereto. After the addition, the reaction mixture was extracted with ethyl acetate, and the organic layer was concentrated. 200 ml of hexane was added thereto, and the precipitated crystals were recovered by filtration to obtain 7.1 g of 2-(1'-hydroxydecyl)-4-methylphenol.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. concentrationthe organic layer was concentrated
  5. addition200 ml of hexane was added
  6. filtrationthe precipitated crystals were recovered by filtration

Sources & evidence

ORD record
ord-5f3f8d9630ea47b5bede8ed635153d9e
Source dataset
uspto-grants-1991_07
Patent number
US05032487

Reaction notes

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