Acetic Acid → HCID 15171862, compound

HRID 256857Notes

Reaction equation

HRID 256857 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:8]=[C:9]([C:21]#[C:22][C:23]2([CH3:37])[CH2:28][CH2:27][C:26]3[C:29]([CH3:36])=[C:30]([OH:35])[C:31]([CH3:34])=[C:32]([CH3:33])[C:25]=3[O:24]2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)C.C(O)(=O)C>CO>[OH:6][C:7]1[CH:8]=[C:9]([C:21]#[C:22][C:23]2([CH3:37])[CH2:28][CH2:27][C:26]3[C:29]([CH3:36])=[C:30]([OH:35])[C:31]([CH3:34])=[C:32]([CH3:33])[C:25]=3[O:24]2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 15171860HCID 15171860, compound

Product 1

HCID 15171862HCID 15171862, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide, 0.12 g (3 mmol), was added to a solution of 0.47 g (1 mmol) of rac-2-{[3-acetyloxy-4-(phenylmethoxy)phenyl]ethynyl}-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol in 10 ml of methanol. The mixture was stirred under argon for 1.5 hours and was then acidified with glacial acetic acid and partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution. The methylene chloride layer was separated, dried and passed over a pad of silica gel. The filtrate was evaporated and the residue was crystallized from ether/hexane to give colorless crystals with m.p. 103°-106°.

Workup

  1. custompartitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
  2. customThe methylene chloride layer was separated
  3. customdried
  4. customThe filtrate was evaporated
  5. customthe residue was crystallized from ether/hexane
  6. customto give colorless crystals with m.p. 103°-106°

Sources & evidence

ORD record
ord-a95603dc947246ccb2ef492bf11e5573
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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