Hydrochloric Acid → HCID 11043160, compound

HRID 1111190Notes

Reaction equation

HRID 1111190 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]([CH3:16])[C:5]2[O:9][C:8]([CH2:11][C:12]#N)([CH3:10])[CH2:7][C:6]=2[C:14]=1[CH3:15].[OH-:18].[Na+].Cl.C[OH:22]>O>[OH:1][C:2]1[C:3]([CH3:17])=[C:4]([CH3:16])[C:5]2[O:9][C:8]([CH2:11][C:12]([OH:22])=[O:18])([CH3:10])[CH2:7][C:6]=2[C:14]=1[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 15086720HCID 15086720, compound

Product 1

HCID 11043160HCID 11043160, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-hydroxy-2-cyanomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran in methanol (5 ml) was added a solution of sodium hydroxide (0.5 g) in water (5 ml). The mixture was heated for three hours under reflux under argon atmosphere. The reaction mixture was cooled to 0° C. neutralized with 2N-HCl. The reaction product was extracted with ethyl acetate. The extract solution was washed with water, dried and concentrated, and then crystallized from ethyl acetate - isopropyl ether to afford the desired 2-(5-hydroxy-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-yl)acetic acid (Compound 1) (0.1 g).

Workup

  1. temperatureThe mixture was heated for three hours
  2. temperatureunder reflux under argon atmosphere
  3. extractionThe reaction product was extracted with ethyl acetate
  4. washThe extract solution was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customcrystallized from ethyl acetate - isopropyl ether

Sources & evidence

ORD record
ord-d63772dde56d4c2e852da22c9279ed92
Source dataset
uspto-grants-1990_12
Patent number
US04978761

Reaction notes

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