4-Hydroxybenzyl Alcohol → (4-(Prop-2-en-1-yloxy)phenyl)methanol

HRID 580980Notes

Reaction equation

HRID 580980 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.CCCCCC.C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 11744970(4-(Prop-2-en-1-yloxy)phenyl)methanolYield 78.4%

Reagents, catalysts & solvents 3

HCID 6569Methyl Ethyl KetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of formula 2 (Z=trifluoromethylsulphonyloxy), methyl 3-(3-allyl-4-trifluoromethylsulphonyloxyphenyl)methyloxyacetate, was prepared as follows. Allyl bromide (4.4 g) was added to a stirred suspension of 4-hydroxybenzyl alcohol (4.34 g) and potassium carbonate (5.00 g) in butanone (40 ml). The reaction mixture was heated at reflux for 18 hours. The reaction mixture was cooled and then filtered. The filtrate was evaporated to give an oil which was purifed by flash column chromatography on silica gel using a 4:1 (v/v) mixture of hexane and ethyl acetate as eluent to give 4-allyloxybenzyl alcohol (4.50 g) as a pale yellow oil; NMR(CDCl3): 1.81(1H,t), 4.48-4.65(4H,m), 5.22-5.48(2H,m), 6.05(1H,m), 6.90(2H,m) and 7.25(2H,m), m/z 164(H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customto give an oil which

Sources & evidence

ORD record
ord-98b009c8bb724779a2198179127c7fea
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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