Hydrochloric Acid → HCID 21523910, compound

HRID 1988184Notes

Reaction equation

HRID 1988184 reaction equation
[H-].[Na+].[OH:3][C:4]1C=C(C)C=C[C:5]=1C(=O)C.[C:14](=[O:21])([O:18][CH2:19][CH3:20])OCC.Cl.[C:23]1([CH3:29])[CH:28]=[CH:27]C=C[CH:24]=1>>[OH:3][C:4]1[C:14](=[O:21])[O:18][C:19]2[C:20]([CH:5]=1)=[CH:27][CH:28]=[C:23]([CH3:29])[CH:24]=2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1140Toluene3×HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 813382'-Hydroxy-4'-methylacetophenone2×

Product 1

HCID 21523910HCID 21523910, compound

Procedure

To a 80° C. suspension of NaH (60 g, 1500 mmol, 60%) in toluene was added 1-(2-hydroxy-4-methylphenyl)ethanone (100 g, 666 mmol; also known as 2′-hydroxy-4′-methylacetophenone) in 800 mL of toluene over 1 h. This was followed by the dropwise addition of diethyl carbonate (157 g, 1.3 mol) in 1000 ml of toluene over 1 h. The reaction mixture was left at 80° C. overnight. After cooling to rt, the solution was poured into 1.6 L of HCl (2N). The precipitate formed was filtered, collected and stirred in MeOH (minimum amount). After filtration, the title compound was dried overnight (at 55° C., under high vacuum) to yield the title compound. 1H NMR (400 MHz, DMSO-d6): δ 12.45 (1H, s), 7.58 (1H, d), 7.13 (2H, m), 6.53 (1H, s) and 2.39 (3H, s).

Workup

  1. customover 1 h
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customcollected
  5. filtrationAfter filtration
  6. dry with materialthe title compound was dried overnight (at 55° C., under high vacuum)

Sources & evidence

ORD record
ord-6a2dc7a3067746e4907541849cfb129c
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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