Hydrochloric Acid → HCID 118021354, compound

HRID 1484505Notes

Reaction equation

HRID 1484505 reaction equation
[C:1]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:14]COC)[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].Cl>CO>[C:1]([CH:5]1[C:13]2[C:12]([OH:14])=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7][O:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90023452HCID 90023452, compound2×

Product 1

HCID 118021354HCID 118021354, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-tert-butyl-7-(methoxymethoxy)-1,3-dihydroisobenzofuran (Intermediate 4, 260 mg, 1.10 mmol) in Methanol (10 mL) a 6N aqueous solution of hydrogen chloride (0.18 ml, 1.10 mmol) was added and the reaction mixture was stirred for 10 hours at 50° C. Volatiles were removed under reduced pressure and the residue was partitioned between water (10 ml) and ethyl acetate (20 ml). The organic layer was dried (Na2SO4), filtered and evaporated affording the title compound (220 mg) as white solid.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue was partitioned between water (10 ml) and ethyl acetate (20 ml)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a500936e73c44347af8391670818cf96
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

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