Hydrochloric Acid → 3-(4-Benzyloxyphenyl)propionic acid

HRID 1942574Notes

Reaction equation

HRID 1942574 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C1COCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 103943-(4-Hydroxyphenyl)propionic acid

Product 1

HCID 5613723-(4-Benzyloxyphenyl)propionic acidYield 100%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-(4-hydroxyphenyl)propionic acid (20.0 g, 0.12 mol) and benzyl bromide (21.5 mL, 0.18 mol) in 155 mL of THF is added, at ambient temperature to a 1N aqueous solution of soda (301 mL). The phase transfer catalyst, Bu4NHSO4 (155 mg, 0.45 mmol), is finally added. The reaction medium is stirred overnight before being heated for 1 h at 80° C. After cooling down, 150 mL of a 1N aqueous solution of HCl is added slowly. After extraction with CH2Cl2, the organic phases are dried over MgSO4, filtered and concentrated under vacuum. Purification is carried out on silica gel (CH2Cl2 up to CH2Cl2/MeOH 95:5) in order to produce compound 2 (30.4 g, 0.12 mol, 99%) in the form of a white solid.

Workup

  1. temperatureAfter cooling down
  2. extractionAfter extraction with CH2Cl2
  3. dry with materialthe organic phases are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification

Sources & evidence

ORD record
ord-c281df435f304bf3b9e60de5347ed913
Source dataset
uspto-grants-2013_03
Patent number
US08389569B2

Reaction notes

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