Water → 1092448-34-4

HRID 1047862Notes

Reaction equation

HRID 1047862 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.O.[OH-].[Na+].Cl[CH:16]([F:18])[F:17]>O1CCOCC1.CCOCC>[F:17][CH:16]([F:18])[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 701334-Hydroxy-2-methylacetophenone

Product 1

HCID 578251511092448-34-4Yield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred suspension of 1-(4-hydroxy-2-methyl-phenyl)-ethanone (15 g, 100 mmol) in dioxane (30 mL) is added water (25 mL) followed by the addition of NaOH (20 g, 500 mmol). Reaction is heated to 65° C. and passed gaseous chlorodifluoromethane (30 g, 150 mmol) using a glass tube dipped below the solution level for 75 minutes. Stirred for 30 min longer and left at RT over the weekend. Water (100 mL) and ether (40 mL) are added after transferring to a reparatory funnel. A semi-gelatinous material settled at the bottom of the aqueous layer after some time. The bottom aqueous layer is drained off and extracted with ether (2×40 mL). The combined ether layers are washed with water (5×25 mL), dried over solid K2SO4, evaporated and distilled (0.04 mm Hg, 61-64° C.) to afford 1-(4-difluoromethoxy-2-methyl-phenyl)-ethanone (A4) (16.2 g, 81%). Rf in tlc 0.60 with ether.

Workup

  1. customReaction
  2. waitleft at RT over the weekend
  3. customafter transferring to a reparatory funnel
  4. extractionextracted with ether (2×40 mL)
  5. washThe combined ether layers are washed with water (5×25 mL)
  6. dry with materialdried over solid K2SO4
  7. customevaporated
  8. distillationdistilled (0.04 mm Hg, 61-64° C.)

Sources & evidence

ORD record
ord-62e0297432244a63a0a764499a44e782
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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