Sulfuric Acid → HCID 16762790, compound

HRID 1773068Notes

Reaction equation

HRID 1773068 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]12(O)[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>ClCCl.O.C(O)(=O)C>[C:12]12([C:8]3[C:9]([OH:11])=[CH:10][C:2]([OH:1])=[C:3]([CH:7]=3)[C:4]([OH:6])=[O:5])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14912,4-Dihydroxybenzoic AcidHCID 641521-AdamantanolHCID 516892Sodium Bicarbonate

Product 1

HCID 16762790HCID 16762790, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2,4-Dihydroxybenzoic acid (9.24 g) and 1-adamantanol (9.14 g) are dissolved in dichloromethane (200 mL) and then stirred. After adding acetic acid (17.1 mL) mixed with concentrated sulfuric acid (3.3 mL) dropwise, the mixture is stirred at room temperature for 12 hours. After adding water (200 mL), sodium bicarbonate is added until the pH of the solution becomes 6. The produced solid is filtered to obtain 8.82 g of 5-adamantan-1-yl-2,4-dihydroxybenzoic acid as solid of a light color.

Workup

  1. stirringthe mixture is stirred at room temperature for 12 hours
  2. additionis added until the pH of the solution
  3. filtrationThe produced solid is filtered

Sources & evidence

ORD record
ord-b92fd6b39cc943b19627b04a9f3e079f
Source dataset
uspto-grants-2016_02
Patent number
US09254251B2

Reaction notes

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