4-Hydroxybenzyl Alcohol → 4-(3-tert-Butyl-4-methoxybenzoyloxymethyl)phenol

HRID 2294583

Reaction equation

HRID 2294583 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:16]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23](Cl)=[O:24])([CH3:19])([CH3:18])[CH3:17].O>C1COCC1>[C:16]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)=[O:24])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 962WaterHCID 1049PyridineHCID 136335553-Tert-butyl-4-methoxybenzoyl chloride

Product 1

HCID 214745304-(3-tert-Butyl-4-methoxybenzoyloxymethyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.24 g (0.01 mol) of 4-hydroxybenzenemethanol, 1 ml (0.01 mol) of pyridine and 50 ml of THF are introduced into a round-bottomed flask. While cooling in an icebath, a solution of 2.2 g (0.01 mol) of 3-tert-butyl-4-methoxybenzoyl chloride in 50 ml of THF is introduced dropwise and the mixture is stirred at room temperature for 24 h. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and ethyl ether (97:3).

Workup

  1. temperatureWhile cooling in an icebath
  2. extractionthe mixture is extracted with ethyl ether
  3. customthe organic phase is separated after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and ethyl ether (97:3)

Sources & evidence

ORD record
ord-99c9e2ac08dd46ac9cb754803fb7d470
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Linked notes

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