Hydrochloric Acid → 7-Tert-butyl-chroman-4-ol

HRID 2092144

Reaction equation

HRID 2092144 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[O:8][CH2:9][CH2:10][CH:11]1[O:16]CCCO1)([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1.C(OCC)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:17]([CH:11]([OH:16])[CH2:10][CH2:9][O:8]2)=[CH:18][CH:19]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 595485522-[2-(3-Tert-butyl-phenoxy)-ethyl]-[1,3]dioxane

Product 1

HCID 595485267-Tert-butyl-chroman-4-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The intermediate from step A was dissolved in 20 ml tetrahydrofuran. Concentrated hydrochloric acid (20 mL) was added, and the reaction mixture was stirred at ambient temperature for 4 hours, diluted with diethyl ether and washed with water. The isolated organic layer was dried with magnesium sulfate, filtered and the solvent removed under reduced pressure to give 2.87 g of crude 7-tert-butyl-chroman-4-ol which was used without further purification.

Workup

  1. washwashed with water
  2. dry with materialThe isolated organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6c7e8dd576bd4647ba727bb644ad6e07
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Linked notes

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