Ethanol → HCID 59439471, compound

HRID 1640074Notes

Reaction equation

HRID 1640074 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[CH2:15][CH2:16][OH:17].[CH2:18]([OH:20])[CH3:19].C1(C)C=CC=CC=1>C(O)(=O)C.O>[C:18]([O:17][CH2:16][CH2:15][C:8]1[C:9]([O:13][CH3:14])=[CH:10][CH:11]=[CH:12][C:7]=1[OH:6])(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 12862427HCID 12862427, compound

Product 1

HCID 59439471HCID 59439471, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1.0 mL (1.8 g, 18 mmol) of concentrated sulfuric acid was added dropwise to a solution of 0.27 g (1.6 mmol) of 2-(2-hydroxy-6-methoxyphenyl)ethanol in 5.0 mL of acetic acid while being cooled on an ice-water bath. This mixture was stirred under room temperature for 5 minutes and 6.0 mL (4.7 g, 102 mmol) of ethanol was added dropwise thereto. 20 mL of toluene and 20 mL of water were added to this mixture and after stirred for 5 minutes, the mixture was transferred to a separatory funnel and settled. The aqueous layer was separated and discarded and after the organic layer was washed with 100 mL of water twice, the solvent was evaporated to obtain 0.16 g of the title compound.

Workup

  1. temperaturewhile being cooled on an ice-water bath
  2. stirringafter stirred for 5 minutes
  3. customthe mixture was transferred to a separatory funnel
  4. customThe aqueous layer was separated
  5. washafter the organic layer was washed with 100 mL of water twice
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-abe47607f7fd48acbd16164ca438cdfc
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

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