Hydrochloric Acid → HCID 10447045, compound

HRID 1940217Notes

Reaction equation

HRID 1940217 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]([OH:14])=[O:13])[C:6]=2[C:15]=1[CH3:16].[C:19](OC(=O)C)(=[O:21])[CH3:20].O.Cl>N1C=CC=CC=1>[C:19]([O:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]([OH:14])=[O:13])[C:6]=2[C:15]=1[CH3:16])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 10131175HCID 10131175, compound

Product 1

HCID 10447045HCID 10447045, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-carboxylic acid (25.03 g, 100 mmol) in pyridine (200 mL) is added acetic anhydride (100 mL) and the mixture is stirred at room temperature for 24 hrs. Water and ice are added and the mixture is stirred at about 30° C. for 30 min. The mixture is cooled in ice and 6N hydrochloric acid (450 mL) is added. The resulting solid is collected, washed with water, taken up in ethyl acetate. The organic layer is washed with 2N hydrochloric acid and water, dried (sodium sulfate) and evaporated to dryness. Recrystallization from ethyl acetate gave 23.6 g (81%) of 5-acetoxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-carboxylic acid (mp=187° C.-188° C.).

Workup

  1. stirringthe mixture is stirred at about 30° C. for 30 min
  2. temperatureThe mixture is cooled in ice
  3. customThe resulting solid is collected
  4. washwashed with water
  5. washThe organic layer is washed with 2N hydrochloric acid and water
  6. dry with materialdried (sodium sulfate)
  7. customevaporated to dryness
  8. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-11d2f3012a3f4018b58f925b6d1e2f86
Source dataset
uspto-grants-1997_12
Patent number
US05698696

Reaction notes

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