Methanol → 4,6-Di-t-butyl-5-hydroxy-2-methoxycarbonyl-2-methyl-2,3-dihydrobenzofuran

HRID 367303Notes

Reaction equation

HRID 367303 reaction equation
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:17])([C:14]([OH:16])=[O:15])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[O:22][Si](C)(C)C)([CH3:4])([CH3:3])[CH3:2].[CH3:27]O>Cl>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([C:14]([O:16][CH3:27])=[O:15])([CH3:17])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 232880354,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid

Product 1

HCID 154857274,6-Di-t-butyl-5-hydroxy-2-methoxycarbonyl-2-methyl-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In 5 ml of a saturated solution of hydrogen chloride in methanol was dissolved 0.20 g of 4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid at room temperature and the mixture was stirred for 3 hours, then the reaction solution was concentrated. The residue was purified on a short column of silica gel eluting with n-hexane containing 16% ethyl acetate to give 0.15 g of 4,6-di-t-butyl-5-hydroxy-2-methoxycarbonyl-2-methyl-2,3-dihydrobenzofuran as a colorless powder.

Workup

  1. concentrationthe reaction solution was concentrated
  2. customThe residue was purified on a short column of silica gel eluting with n-hexane containing 16% ethyl acetate

Sources & evidence

ORD record
ord-bd37db729642412a9fcba01266ebdae3
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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