Triethylamine → 2,6-Di-tert-butyl-4-[(2-hydroxyethyl)sulfanyl]phenol

HRID 487899Notes

Reaction equation

HRID 487899 reaction equation
C(N(CC)CC)C.Br[CH2:9][CH2:10][OH:11].[CH3:12][C:13]([C:16]1[CH:21]=[C:20]([SH:22])[CH:19]=[C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]=1[OH:27])([CH3:15])[CH3:14].C(OCC)(=O)C>C(Cl)Cl>[CH3:24][C:23]([C:18]1[CH:19]=[C:20]([S:22][CH2:9][CH2:10][OH:11])[CH:21]=[C:16]([C:13]([CH3:12])([CH3:14])[CH3:15])[C:17]=1[OH:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 108982-BromoethanolHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 140118152,6-Di-tert-butyl-4-[(2-hydroxyethyl)sulfanyl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.42 g, 0.0042 mole), 2-bromoethanol (0.52 g, 0.0044 mole) and the title compound of Example 2 (1.0 g, 0.0042 mole) were stirred in methylene chloride (50 ml) for 20 hours. The reaction was condensed and ethyl acetate (25 ml) added to the residue. After filtering the white solid the filtrate was concentrated and the product purified by chromatography on silica, m.p. ca. 66° C.

Workup

  1. additionadded to the residue
  2. filtrationAfter filtering the white solid the filtrate
  3. concentrationwas concentrated
  4. customthe product purified by chromatography on silica, m.p. ca. 66° C.

Sources & evidence

ORD record
ord-ba6b21d69aee4c3ba73fc35db0b8a3ac
Source dataset
uspto-grants-1994_03
Patent number
US05298514

Reaction notes

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