Sodium Hydroxide → 3-[4-(Hydroxymethyl)phenyl]propanoic acid

HRID 2083112Notes

Reaction equation

HRID 2083112 reaction equation
Cl[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+].C1C=C(C(C2C=CC(O)=CC=2)C2C=CC([OH:29])=CC=2)C(C(O)=O)=CC=1>O>[OH:29][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 66494PhenolphthalinHCID 2032212856703-33-4

Product 1

HCID 203221243-[4-(Hydroxymethyl)phenyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g (0.15 mol) of 4-chloromethyl-hydrocinnamic acid (J. Org, Chem. 26, 148 (1961) in 200 ml of water were neutralized with a 10% sodium hydroxide solution against phenol phthaline. 10% of NaOH (on the whole about 60 ml) were added dropwise, while stirring at reflux temperature, to the solution obtained in the same measure as it was consumed. When the reaction was finished, the mixture was saturated with sodium chloride, acidified with concentrated hydrochloric acid, the product precipitated was suction-filtered and washed with water. Melting point: 124° - 126° C.

Workup

  1. temperatureat reflux temperature
  2. customto the solution obtained in the same measure as it
  3. customwas consumed
  4. customthe product precipitated
  5. filtrationwas suction-filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-67ffe46d7bdb4acb84887d3a0e03fa94
Source dataset
uspto-grants-1978_04
Patent number
US04083990

Reaction notes

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